# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Fq20170908_a
_database_code_depnum_ccdc_archive 'CCDC 1580853'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;         
1-acetyl-3-(phenyl)-5-(1-pyrenyl) pyrazoline-formic acid solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C112 H88 N8 O12'
_chemical_formula_weight         1737.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1829(5)
_cell_length_b                   25.6141(16)
_cell_length_c                   18.5826(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.823(2)
_cell_angle_gamma                90
_cell_volume                     4306.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5815
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.52

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38603
_diffrn_reflns_av_unetI/netI     0.1094
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             9175
_reflns_number_gt                4132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²+1.7487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9175
_refine_ls_number_parameters     614
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.2024
_refine_ls_R_factor_gt           0.0884
_refine_ls_wR_factor_ref         0.2595
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0760(4) 0.71949(14) 0.37426(18) 0.0460(9) Uani 1 1 d . . . . .
H1 H 0.0070 0.7400 0.3422 0.055 Uiso 1 1 calc R U . . .
C2 C 0.0829(4) 0.66747(14) 0.3630(2) 0.0519(9) Uani 1 1 d . . . . .
H2 H 0.0158 0.6521 0.3242 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1867(4) 0.63505(14) 0.4072(2) 0.0529(10) Uani 1 1 d . . . . .
C4 C 0.2841(4) 0.65810(14) 0.4662(2) 0.0482(9) Uani 1 1 d . . . . .
C5 C 0.2740(3) 0.71258(13) 0.48078(18) 0.0427(8) Uani 1 1 d . . . . .
C6 C 0.1717(3) 0.74446(13) 0.43403(17) 0.0402(8) Uani 1 1 d . . . . .
C7 C 0.1977(5) 0.58142(16) 0.3948(2) 0.0715(12) Uani 1 1 d . . . . .
H7 H 0.1302 0.5652 0.3569 0.086 Uiso 1 1 calc R U . . .
C8 C 0.3061(6) 0.55169(17) 0.4371(3) 0.0774(13) Uani 1 1 d . . . . .
H8 H 0.3152 0.5157 0.4265 0.093 Uiso 1 1 calc R U . . .
C9 C 0.4002(5) 0.57379(18) 0.4944(3) 0.0725(13) Uani 1 1 d . . . . .
H9 H 0.4731 0.5527 0.5230 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3912(4) 0.62668(15) 0.5114(2) 0.0556(10) Uani 1 1 d . . . . .
C11 C 0.4841(4) 0.65118(19) 0.5718(2) 0.0660(12) Uani 1 1 d . . . . .
H11 H 0.5570 0.6308 0.6017 0.079 Uiso 1 1 calc R U . . .
C12 C 0.4719(4) 0.70160(19) 0.5875(2) 0.0633(11) Uani 1 1 d . . . . .
H12 H 0.5328 0.7158 0.6294 0.076 Uiso 1 1 calc R U . . .
C13 C 0.3681(4) 0.73503(15) 0.54203(19) 0.0497(9) Uani 1 1 d . . . . .
C14 C 0.3591(4) 0.78805(16) 0.5544(2) 0.0557(10) Uani 1 1 d . . . . .
H14 H 0.4200 0.8033 0.5955 0.067 Uiso 1 1 calc R U . . .
C15 C 0.2624(4) 0.81910(14) 0.50769(19) 0.0511(9) Uani 1 1 d . . . . .
H15 H 0.2601 0.8556 0.5167 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1687(3) 0.79845(13) 0.44795(18) 0.0431(8) Uani 1 1 d . . . . .
C17 C 0.0715(4) 0.83416(13) 0.39481(19) 0.0474(9) Uani 1 1 d . . . . .
H17 H -0.0251 0.8166 0.3767 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1452(4) 0.85028(13) 0.32930(19) 0.0488(9) Uani 1 1 d . . . . .
H18A H 0.2434 0.8337 0.3320 0.059 Uiso 1 1 calc R U . . .
H18B H 0.0825 0.8409 0.2823 0.059 Uiso 1 1 calc R U . . .
C19 C 0.1585(4) 0.90832(13) 0.3384(2) 0.0496(9) Uani 1 1 d . . . . .
C20 C -0.0379(5) 0.89158(19) 0.4781(2) 0.072 Uani 1 1 d . . . . .
C21 C -0.0589(9) 0.9429(3) 0.5066(4) 0.166(3) Uani 1 1 d . . . . .
H21A H -0.1315 0.9411 0.5395 0.249 Uiso 1 1 calc R U . . .
H21B H -0.0948 0.9667 0.4661 0.249 Uiso 1 1 calc R U . . .
H21C H 0.0353 0.9558 0.5335 0.249 Uiso 1 1 calc R U . . .
C22 C 0.2276(4) 0.94258(15) 0.2895(2) 0.0601(11) Uani 1 1 d . . . . .
C23 C 0.2000(6) 0.99608(18) 0.2875(3) 0.0889(15) Uani 1 1 d . . . . .
H23 H 0.1371 1.0111 0.3175 0.107 Uiso 1 1 calc R U . . .
C24 C 0.2676(7) 1.0277(2) 0.2398(3) 0.1020(17) Uani 1 1 d . . . . .
H24 H 0.2479 1.0641 0.2368 0.122 Uiso 1 1 calc R U . . .
C25 C 0.3593(6) 1.0064(2) 0.1987(3) 0.0913(15) Uani 1 1 d . . . . .
H25 H 0.4070 1.0282 0.1685 0.110 Uiso 1 1 calc R U . . .
C26 C 0.3848(5) 0.9544(2) 0.1994(2) 0.0797(13) Uani 1 1 d . . . . .
H26 H 0.4487 0.9400 0.1695 0.096 Uiso 1 1 calc R U . . .
C27 C 0.3170(5) 0.92195(17) 0.2444(2) 0.0646(11) Uani 1 1 d . . . . .
H27 H 0.3329 0.8853 0.2438 0.078 Uiso 1 1 calc R U . . .
C28 C 0.5626(5) 0.62536(17) 0.9180(2) 0.0731(12) Uani 1 1 d . . . . .
H28 H 0.5191 0.6479 0.9491 0.088 Uiso 1 1 calc R U . . .
C29 C 0.5596(6) 0.57352(19) 0.9277(3) 0.0915(16) Uani 1 1 d . . . . .
H29 H 0.5103 0.5604 0.9649 0.110 Uiso 1 1 calc R U . . .
C30 C 0.6257(6) 0.53735(17) 0.8857(2) 0.0809(14) Uani 1 1 d . . . . .
C31 C 0.6948(4) 0.55678(15) 0.8284(2) 0.0579(10) Uani 1 1 d . . . . .
C32 C 0.6936(4) 0.61183(14) 0.81522(18) 0.0480(9) Uani 1 1 d . . . . .
C33 C 0.6323(4) 0.64724(14) 0.85997(19) 0.0497(9) Uani 1 1 d . . . . .
C34 C 0.6272(7) 0.48312(19) 0.8966(3) 0.110(2) Uani 1 1 d . . . . .
H34 H 0.5774 0.4691 0.9331 0.132 Uiso 1 1 calc R U . . .
C35 C 0.6979(7) 0.44996(19) 0.8566(3) 0.1086(19) Uani 1 1 d . . . . .
H35 H 0.7016 0.4136 0.8671 0.130 Uiso 1 1 calc R U . . .
C36 C 0.7637(6) 0.46922(17) 0.8008(2) 0.0809(14) Uani 1 1 d . . . . .
H36 H 0.8111 0.4458 0.7726 0.097 Uiso 1 1 calc R U . . .
C37 C 0.7619(4) 0.52235(15) 0.7851(2) 0.0588(10) Uani 1 1 d . . . . .
C38 C 0.8231(4) 0.54448(15) 0.7259(2) 0.0543(10) Uani 1 1 d . . . . .
H38 H 0.8670 0.5217 0.6954 0.065 Uiso 1 1 calc R U . . .
C39 C 0.8213(4) 0.59451(16) 0.7119(2) 0.0540(10) Uani 1 1 d . . . . .
H39 H 0.8624 0.6067 0.6715 0.065 Uiso 1 1 calc R U . . .
C40 C 0.7595(3) 0.63114(14) 0.75577(18) 0.044 Uani 1 1 d . . . . .
C41 C 0.7620(3) 0.68450(14) 0.74385(19) 0.0487(9) Uani 1 1 d . . . . .
H41 H 0.8044 0.6975 0.7042 0.058 Uiso 1 1 calc R U . . .
C42 C 0.7042(4) 0.71916(14) 0.7883(2) 0.0497(9) Uani 1 1 d . . . . .
H42 H 0.7092 0.7556 0.7796 0.060 Uiso 1 1 calc R U . . .
C43 C 0.6375(3) 0.70100(14) 0.84664(19) 0.0470(9) Uani 1 1 d . . . . .
C44 C 0.5865(4) 0.74042(14) 0.8981(2) 0.0547(10) Uani 1 1 d . . . . .
H44 H 0.5017 0.7258 0.9189 0.066 Uiso 1 1 calc R U . . .
C45 C 0.7082(4) 0.75884(14) 0.9603(2) 0.0589(10) Uani 1 1 d . . . . .
H45A H 0.6791 0.7527 1.0085 0.071 Uiso 1 1 calc R U . . .
H45B H 0.8024 0.7404 0.9587 0.071 Uiso 1 1 calc R U . . .
C46 C 0.7227(4) 0.81594(15) 0.9464(2) 0.0548(10) Uani 1 1 d . . . . .
C47 C 0.4302(5) 0.79698(18) 0.8067(3) 0.0677(12) Uani 1 1 d . . . . .
C48 C 0.4121(7) 0.8503(2) 0.7756(3) 0.118(2) Uani 1 1 d . . . . .
H48A H 0.3240 0.8515 0.7376 0.178 Uiso 1 1 calc R U . . .
H48B H 0.4993 0.8595 0.7544 0.178 Uiso 1 1 calc R U . . .
H48C H 0.4010 0.8752 0.8143 0.178 Uiso 1 1 calc R U . . .
C49 C 0.8291(4) 0.85157(15) 0.9902(2) 0.0565(10) Uani 1 1 d . . . . .
C50 C 0.8137(5) 0.90532(17) 0.9827(3) 0.0735(12) Uani 1 1 d . . . . .
H50 H 0.7322 0.9197 0.9504 0.088 Uiso 1 1 calc R U . . .
C51 C 0.9183(6) 0.93803(18) 1.0229(3) 0.0865(16) Uani 1 1 d . . . . .
H51 H 0.9086 0.9748 1.0175 0.104 Uiso 1 1 calc R U . . .
C52 C 1.0355(6) 0.9175(2) 1.0702(3) 0.0829(15) Uani 1 1 d . . . . .
H52 H 1.1066 0.9403 1.0970 0.099 Uiso 1 1 calc R U . . .
C53 C 1.0511(5) 0.8645(2) 1.0794(2) 0.0704(12) Uani 1 1 d . . . . .
H53 H 1.1320 0.8504 1.1125 0.084 Uiso 1 1 calc R U . . .
C54 C 0.9466(4) 0.83158(17) 1.0394(2) 0.0620(11) Uani 1 1 d . . . . .
H54 H 0.9559 0.7949 1.0459 0.074 Uiso 1 1 calc R U . . .
N1 N 0.0452(3) 0.88484(12) 0.42637(17) 0.0562(8) Uani 1 1 d . . . . .
N2 N 0.1027(3) 0.92683(12) 0.39208(19) 0.0595(8) Uani 1 1 d . . . . .
N3 N 0.5439(3) 0.79011(13) 0.86221(18) 0.0599(9) Uani 1 1 d . . . . .
N4 N 0.6287(4) 0.83310(13) 0.8909(2) 0.0665(10) Uani 1 1 d . . . . .
O1 O -0.0942(3) 0.85388(13) 0.50460(16) 0.0870(9) Uani 1 1 d . . . . .
O2 O 0.3553(3) 0.75816(12) 0.78398(17) 0.0749(8) Uani 1 1 d . . . . .
C55 C 0.0697(7) 0.7942(4) 0.6566(3) 0.118(2) Uani 1 1 d . . . . .
H55 H -0.0088 0.7912 0.6163 0.142 Uiso 1 1 calc R U . . .
O3 O 0.1033(7) 0.8383(2) 0.6768(3) 0.1465(18) Uani 1 1 d . . . . .
O4 O 0.1261(4) 0.75203(15) 0.68238(19) 0.0938(10) Uani 1 1 d . . . . .
H4 H 0.2162 0.7515 0.6792 0.141 Uiso 1 1 calc R U . . .
C56A C 0.7618(17) 0.8504(7) 0.6501(7) 0.120(3) Uani 0.541(7) 1 d D U P A 1
H56A H 0.8418 0.8744 0.6587 0.144 Uiso 0.541(7) 1 calc R U P A 1
O5A O 0.6978(10) 0.8385(3) 0.6987(5) 0.121(3) Uani 0.541(7) 1 d D U P A 1
O6A O 0.7228(9) 0.8312(4) 0.5883(5) 0.134(3) Uani 0.541(7) 1 d D U P A 1
H6A H 0.7767 0.8431 0.5599 0.201 Uiso 0.541(7) 1 d R U P A 1
C56B C 0.689(2) 0.8566(6) 0.6459(11) 0.125(4) Uani 0.459(7) 1 d D U P A 2
H56B H 0.6236 0.8693 0.6766 0.150 Uiso 0.459(7) 1 calc R U P A 2
O5B O 0.7409(13) 0.8885(4) 0.6039(6) 0.146(4) Uani 0.459(7) 1 d D U P A 2
H5B H 0.6735 0.8983 0.5702 0.218 Uiso 0.459(7) 1 d R U P A 2
O6B O 0.7202(12) 0.8102(5) 0.6477(7) 0.135(3) Uani 0.459(7) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.352(5) . ?
C1 C6 1.443(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(5) . ?
C2 H2 0.9500 . ?
C3 C7 1.400(5) . ?
C3 C4 1.419(5) . ?
C4 C5 1.428(5) . ?
C4 C10 1.428(5) . ?
C5 C6 1.423(5) . ?
C5 C13 1.428(5) . ?
C6 C16 1.408(5) . ?
C7 C8 1.387(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.434(6) . ?
C11 C12 1.333(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.442(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.519(5) . ?
C17 N1 1.461(4) . ?
C17 C18 1.546(5) . ?
C17 H17 1.0000 . ?
C18 C19 1.499(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N2 1.288(4) . ?
C19 C22 1.481(5) . ?
C20 O1 1.237(5) . ?
C20 N1 1.336(5) . ?
C20 C21 1.443(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.375(5) . ?
C22 C23 1.393(6) . ?
C23 C24 1.420(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.346(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.351(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.399(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.341(6) . ?
C28 C33 1.458(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.414(6) . ?
C29 H29 0.9500 . ?
C30 C34 1.403(6) . ?
C30 C31 1.419(5) . ?
C31 C37 1.406(5) . ?
C31 C32 1.431(5) . ?
C32 C33 1.411(5) . ?
C32 C40 1.435(5) . ?
C33 C43 1.401(5) . ?
C34 C35 1.364(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.377(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.392(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.433(5) . ?
C38 C39 1.307(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.423(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.385(5) . ?
C41 C42 1.379(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.411(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.519(5) . ?
C44 N3 1.459(5) . ?
C44 C45 1.539(5) . ?
C44 H44 1.0000 . ?
C45 C46 1.495(5) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 N4 1.303(5) . ?
C46 C49 1.476(5) . ?
C47 O2 1.242(5) . ?
C47 N3 1.348(5) . ?
C47 C48 1.481(7) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 C50 1.388(6) . ?
C49 C54 1.388(6) . ?
C50 C51 1.392(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.373(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.375(6) . ?
C52 H52 0.9500 . ?
C53 C54 1.393(5) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
N1 N2 1.399(4) . ?
N3 N4 1.401(4) . ?
C55 O3 1.214(7) . ?
C55 O4 1.257(7) . ?
C55 H55 0.9500 . ?
O4 H4 0.8400 . ?
C56A O5A 1.197(12) . ?
C56A O6A 1.244(14) . ?
C56A H56A 0.9500 . ?
O6A H6A 0.8400 . ?
C56B O6B 1.224(16) . ?
C56B O5B 1.279(15) . ?
C56B H56B 0.9500 . ?
O5B H5B 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 122.2(3) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C7 C3 C2 122.7(4) . . ?
C7 C3 C4 118.8(4) . . ?
C2 C3 C4 118.5(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 C10 120.0(4) . . ?
C5 C4 C10 120.0(3) . . ?
C6 C5 C13 120.2(3) . . ?
C6 C5 C4 120.2(3) . . ?
C13 C5 C4 119.7(3) . . ?
C16 C6 C5 118.9(3) . . ?
C16 C6 C1 123.3(3) . . ?
C5 C6 C1 117.9(3) . . ?
C8 C7 C3 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C3 C7 H7 119.7 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.5(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C4 118.3(4) . . ?
C9 C10 C11 123.5(4) . . ?
C4 C10 C11 118.2(4) . . ?
C12 C11 C10 122.3(4) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C5 118.9(3) . . ?
C14 C13 C12 122.6(4) . . ?
C5 C13 C12 118.5(4) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 121.8(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C6 119.5(3) . . ?
C15 C16 C17 120.4(3) . . ?
C6 C16 C17 120.0(3) . . ?
N1 C17 C16 113.1(3) . . ?
N1 C17 C18 101.7(3) . . ?
C16 C17 C18 112.7(3) . . ?
N1 C17 H17 109.7 . . ?
C16 C17 H17 109.7 . . ?
C18 C17 H17 109.7 . . ?
C19 C18 C17 102.4(3) . . ?
C19 C18 H18A 111.3 . . ?
C17 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C17 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
N2 C19 C22 121.7(3) . . ?
N2 C19 C18 114.6(3) . . ?
C22 C19 C18 123.7(3) . . ?
O1 C20 N1 121.0(4) . . ?
O1 C20 C21 118.3(5) . . ?
N1 C20 C21 120.7(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 119.1(4) . . ?
C27 C22 C19 120.6(4) . . ?
C23 C22 C19 120.3(4) . . ?
C22 C23 C24 118.8(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 121.2(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C27 119.9(5) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.6(4) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C33 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C33 C28 H28 119.9 . . ?
C28 C29 C30 123.7(4) . . ?
C28 C29 H29 118.2 . . ?
C30 C29 H29 118.2 . . ?
C34 C30 C29 124.3(4) . . ?
C34 C30 C31 117.5(4) . . ?
C29 C30 C31 118.3(4) . . ?
C37 C31 C30 120.4(4) . . ?
C37 C31 C32 120.8(3) . . ?
C30 C31 C32 118.9(4) . . ?
C33 C32 C31 121.7(3) . . ?
C33 C32 C40 119.7(3) . . ?
C31 C32 C40 118.7(3) . . ?
C43 C33 C32 119.9(3) . . ?
C43 C33 C28 122.8(3) . . ?
C32 C33 C28 117.3(3) . . ?
C35 C34 C30 122.1(5) . . ?
C35 C34 H34 119.0 . . ?
C30 C34 H34 119.0 . . ?
C34 C35 C36 119.9(4) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C37 121.2(4) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C36 C37 C31 118.9(4) . . ?
C36 C37 C38 123.8(4) . . ?
C31 C37 C38 117.3(3) . . ?
C39 C38 C37 123.2(4) . . ?
C39 C38 H38 118.4 . . ?
C37 C38 H38 118.4 . . ?
C38 C39 C40 121.7(4) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 H39 119.2 . . ?
C41 C40 C39 122.7(3) . . ?
C41 C40 C32 118.9(3) . . ?
C39 C40 C32 118.4(3) . . ?
C42 C41 C40 121.4(3) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C41 C42 C43 120.6(3) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C33 C43 C42 119.5(3) . . ?
C33 C43 C44 121.2(3) . . ?
C42 C43 C44 119.0(3) . . ?
N3 C44 C43 112.3(3) . . ?
N3 C44 C45 100.4(3) . . ?
C43 C44 C45 114.5(3) . . ?
N3 C44 H44 109.8 . . ?
C43 C44 H44 109.8 . . ?
C45 C44 H44 109.8 . . ?
C46 C45 C44 104.1(3) . . ?
C46 C45 H45A 110.9 . . ?
C44 C45 H45A 110.9 . . ?
C46 C45 H45B 110.9 . . ?
C44 C45 H45B 110.9 . . ?
H45A C45 H45B 108.9 . . ?
N4 C46 C49 120.9(4) . . ?
N4 C46 C45 113.6(4) . . ?
C49 C46 C45 125.4(4) . . ?
O2 C47 N3 117.9(4) . . ?
O2 C47 C48 125.9(5) . . ?
N3 C47 C48 116.1(4) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 C54 119.1(4) . . ?
C50 C49 C46 120.8(4) . . ?
C54 C49 C46 120.1(4) . . ?
C49 C50 C51 119.6(5) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C52 C51 C50 120.5(5) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C51 C52 C53 120.7(5) . . ?
C51 C52 H52 119.6 . . ?
C53 C52 H52 119.6 . . ?
C52 C53 C54 119.0(5) . . ?
C52 C53 H53 120.5 . . ?
C54 C53 H53 120.5 . . ?
C49 C54 C53 121.1(4) . . ?
C49 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C20 N1 N2 122.3(3) . . ?
C20 N1 C17 123.9(4) . . ?
N2 N1 C17 113.5(3) . . ?
C19 N2 N1 107.5(3) . . ?
C47 N3 N4 119.8(4) . . ?
C47 N3 C44 125.2(3) . . ?
N4 N3 C44 115.1(3) . . ?
C46 N4 N3 106.6(3) . . ?
O3 C55 O4 128.0(6) . . ?
O3 C55 H55 116.0 . . ?
O4 C55 H55 116.0 . . ?
C55 O4 H4 109.5 . . ?
O5A C56A O6A 119.5(15) . . ?
O5A C56A H56A 120.2 . . ?
O6A C56A H56A 120.2 . . ?
C56A O6A H6A 109.2 . . ?
O6B C56B O5B 121.7(17) . . ?
O6B C56B H56B 119.2 . . ?
O5B C56B H56B 119.2 . . ?
C56B O5B H5B 109.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6A H6A O1 0.84 1.72 2.544(9) 167.1 1_655
C56A H56A O3 0.95 2.54 3.106(16) 118.2 1_655
O4 H4 O2 0.84 2.15 2.581(5) 112.1 .
C55 H55 O6A 0.95 2.64 3.358(11) 133.0 1_455
C55 H55 O1 0.95 2.64 3.336(7) 130.9 .
C48 H48B O5A 0.98 2.31 3.209(10) 152.4 .
C48 H48A O3 0.98 2.17 3.120(9) 162.4 .
C45 H45A O6A 0.99 2.60 3.300(10) 127.4 4_576
C21 H21A O5B 0.98 2.26 3.119(13) 146.1 1_455

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.053

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fq9005_a
_database_code_depnum_ccdc_archive 'CCDC 1580854'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;         
1-acetyl-3-(phenyl)-5-(1-pyrenyl) pyrazoline-propanoic acid solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 N2 O3'
_chemical_formula_weight         462.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.5529(18)
_cell_length_b                   25.439(5)
_cell_length_c                   8.9279(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2396.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7548
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.94

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20995
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             5269
_reflns_number_gt                3608
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.917
_reflns_Friedel_fraction_full    0.942

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5269
_refine_ls_number_parameters     320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5452(2) 0.57301(11) 0.4809(3) 0.0539(7) Uani 1 1 d . . . . .
H1 H 0.5945 0.5490 0.5336 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5771(3) 0.62440(12) 0.4825(4) 0.0672(8) Uani 1 1 d . . . . .
H2 H 0.6475 0.6348 0.5377 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5071(3) 0.66320(11) 0.4026(3) 0.0637(8) Uani 1 1 d . . . . .
C4 C 0.4007(3) 0.64699(10) 0.3197(3) 0.0540(7) Uani 1 1 d . . . . .
C5 C 0.3654(2) 0.59251(9) 0.3165(3) 0.0435(6) Uani 1 1 d . . . . .
C6 C 0.4365(2) 0.55469(9) 0.3994(3) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.5394(4) 0.71679(13) 0.4022(5) 0.0917(11) Uani 1 1 d . . . . .
H7 H 0.6099 0.7281 0.4557 0.110 Uiso 1 1 calc R U . . .
C8 C 0.4680(5) 0.75271(14) 0.3234(5) 0.1051(14) Uani 1 1 d . . . . .
H8 H 0.4903 0.7881 0.3249 0.126 Uiso 1 1 calc R U . . .
C9 C 0.3646(5) 0.73679(13) 0.2429(5) 0.0928(12) Uani 1 1 d . . . . .
H9 H 0.3177 0.7618 0.1909 0.111 Uiso 1 1 calc R U . . .
C10 C 0.3275(3) 0.68432(11) 0.2367(3) 0.0661(8) Uani 1 1 d . . . . .
C11 C 0.2215(3) 0.66615(13) 0.1517(4) 0.0709(9) Uani 1 1 d . . . . .
H11 H 0.1738 0.6903 0.0976 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1892(2) 0.61579(12) 0.1477(3) 0.0615(7) Uani 1 1 d . . . . .
H12 H 0.1202 0.6054 0.0899 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2587(2) 0.57689(9) 0.2310(3) 0.0475(6) Uani 1 1 d . . . . .
C14 C 0.2257(2) 0.52388(10) 0.2296(3) 0.0520(6) Uani 1 1 d . . . . .
H14 H 0.1569 0.5128 0.1726 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2933(2) 0.48767(9) 0.3112(3) 0.0484(6) Uani 1 1 d . . . . .
H15 H 0.2686 0.4526 0.3088 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3972(2) 0.50193(9) 0.3970(3) 0.0412(5) Uani 1 1 d . . . . .
C17 C 0.4675(2) 0.45986(9) 0.4853(3) 0.0458(6) Uani 1 1 d . . . . .
H17 H 0.5139 0.4760 0.5685 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5574(2) 0.42563(9) 0.3918(3) 0.0497(6) Uani 1 1 d . . . . .
H18A H 0.5575 0.4365 0.2877 0.060 Uiso 1 1 calc R U . . .
H18B H 0.6432 0.4273 0.4304 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5031(2) 0.37136(9) 0.4089(3) 0.0491(6) Uani 1 1 d . . . . .
C20 C 0.2857(2) 0.42975(11) 0.6415(3) 0.0532(6) Uani 1 1 d . . . . .
C21 C 0.1974(3) 0.38623(12) 0.6797(4) 0.0728(9) Uani 1 1 d . . . . .
H21A H 0.1377 0.3981 0.7533 0.109 Uiso 1 1 calc R U . . .
H21B H 0.2447 0.3571 0.7191 0.109 Uiso 1 1 calc R U . . .
H21C H 0.1529 0.3753 0.5912 0.109 Uiso 1 1 calc R U . . .
C22 C 0.5579(3) 0.32318(11) 0.3451(3) 0.0558(7) Uani 1 1 d . . . . .
C23 C 0.5097(3) 0.27436(12) 0.3817(4) 0.0760(9) Uani 1 1 d . . . . .
H23 H 0.4389 0.2718 0.4432 0.091 Uiso 1 1 calc R U . . .
C24 C 0.5668(4) 0.22922(14) 0.3268(5) 0.0985(12) Uani 1 1 d . . . . .
H24 H 0.5341 0.1964 0.3516 0.118 Uiso 1 1 calc R U . . .
C25 C 0.6695(4) 0.23265(18) 0.2376(6) 0.1127(15) Uani 1 1 d . . . . .
H25 H 0.7079 0.2022 0.2023 0.135 Uiso 1 1 calc R U . . .
C26 C 0.7176(4) 0.28087(18) 0.1987(6) 0.1199(17) Uani 1 1 d . . . . .
H26 H 0.7877 0.2831 0.1359 0.144 Uiso 1 1 calc R U . . .
C27 C 0.6621(3) 0.32582(13) 0.2527(5) 0.0842(10) Uani 1 1 d . . . . .
H27 H 0.6953 0.3584 0.2265 0.101 Uiso 1 1 calc R U . . .
N1 N 0.3786(2) 0.41976(8) 0.5430(2) 0.0498(5) Uani 1 1 d . . . . .
N2 N 0.4036(2) 0.36906(8) 0.4915(3) 0.0519(5) Uani 1 1 d . . . . .
O1 O 0.27671(18) 0.47516(8) 0.6919(2) 0.0644(5) Uani 1 1 d . . . . .
C28 C 0.0141(5) 0.60897(19) 0.5423(4) 0.1229(17) Uani 1 1 d . . . . .
H28A H -0.0761 0.6054 0.5518 0.184 Uiso 1 1 calc R U . . .
H28B H 0.0368 0.6091 0.4382 0.184 Uiso 1 1 calc R U . . .
H28C H 0.0407 0.6414 0.5877 0.184 Uiso 1 1 calc R U . . .
C29 C 0.0776(3) 0.56400(12) 0.6188(4) 0.0675(8) Uani 1 1 d . . . . .
H29A H 0.1686 0.5677 0.6072 0.081 Uiso 1 1 calc R U . . .
H29B H 0.0525 0.5316 0.5698 0.081 Uiso 1 1 calc R U . . .
C30 C 0.0473(3) 0.56002(11) 0.7813(3) 0.0587(7) Uani 1 1 d . . . . .
O2 O 0.1052(2) 0.52166(8) 0.8563(2) 0.0728(6) Uani 1 1 d . . . . .
H2A H 0.1518 0.5054 0.7994 0.109 Uiso 1 1 calc R U . . .
O3 O -0.0256(2) 0.58843(9) 0.8452(3) 0.0846(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.350(4) . ?
C1 C6 1.436(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.425(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(4) . ?
C3 C7 1.406(4) . ?
C4 C10 1.431(4) . ?
C4 C5 1.435(3) . ?
C5 C13 1.417(3) . ?
C5 C6 1.427(3) . ?
C6 C16 1.405(3) . ?
C7 C8 1.377(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.429(5) . ?
C11 C12 1.326(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.439(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.522(3) . ?
C17 N1 1.479(3) . ?
C17 C18 1.534(4) . ?
C17 H17 0.9800 . ?
C18 C19 1.502(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N2 1.285(3) . ?
C19 C22 1.470(4) . ?
C20 O1 1.243(3) . ?
C20 N1 1.341(3) . ?
C20 C21 1.487(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.377(4) . ?
C22 C23 1.381(4) . ?
C23 C24 1.386(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.347(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N1 N2 1.394(3) . ?
C28 C29 1.492(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.489(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 O3 1.200(3) . ?
C30 O2 1.332(3) . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.3(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 122.4(3) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C7 118.5(3) . . ?
C4 C3 C2 118.3(2) . . ?
C7 C3 C2 123.2(3) . . ?
C3 C4 C10 120.6(2) . . ?
C3 C4 C5 120.0(2) . . ?
C10 C4 C5 119.4(3) . . ?
C13 C5 C6 120.5(2) . . ?
C13 C5 C4 119.2(2) . . ?
C6 C5 C4 120.3(2) . . ?
C16 C6 C5 118.7(2) . . ?
C16 C6 C1 123.6(2) . . ?
C5 C6 C1 117.7(2) . . ?
C8 C7 C3 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C3 C7 H7 119.6 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.9(4) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 123.5(3) . . ?
C9 C10 C4 117.6(3) . . ?
C11 C10 C4 118.9(3) . . ?
C12 C11 C10 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C5 118.4(2) . . ?
C14 C13 C12 122.3(2) . . ?
C5 C13 C12 119.4(2) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.9(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C6 119.5(2) . . ?
C15 C16 C17 119.2(2) . . ?
C6 C16 C17 121.3(2) . . ?
N1 C17 C16 110.87(19) . . ?
N1 C17 C18 100.95(18) . . ?
C16 C17 C18 114.8(2) . . ?
N1 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
C18 C17 H17 110.0 . . ?
C19 C18 C17 103.3(2) . . ?
C19 C18 H18A 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C19 C18 H18B 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
N2 C19 C22 120.4(2) . . ?
N2 C19 C18 114.3(2) . . ?
C22 C19 C18 125.2(2) . . ?
O1 C20 N1 118.0(2) . . ?
O1 C20 C21 124.1(3) . . ?
N1 C20 C21 117.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 C19 120.4(3) . . ?
C23 C22 C19 120.9(3) . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 120.7(4) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C20 N1 N2 122.0(2) . . ?
C20 N1 C17 124.2(2) . . ?
N2 N1 C17 113.81(19) . . ?
C19 N2 N1 107.5(2) . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C28 C29 C30 113.7(3) . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29B 108.8 . . ?
C30 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
O3 C30 O2 119.7(3) . . ?
O3 C30 C29 124.1(3) . . ?
O2 C30 C29 116.2(3) . . ?
C30 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C7 -179.6(3) . . . . ?
C7 C3 C4 C10 0.2(4) . . . . ?
C2 C3 C4 C10 -179.6(3) . . . . ?
C7 C3 C4 C5 179.5(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C13 -179.3(2) . . . . ?
C10 C4 C5 C13 0.0(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C10 C4 C5 C6 -179.5(2) . . . . ?
C13 C5 C6 C16 -1.3(3) . . . . ?
C4 C5 C6 C16 178.3(2) . . . . ?
C13 C5 C6 C1 178.7(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C2 C1 C6 C16 -178.4(3) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C4 C3 C7 C8 0.5(5) . . . . ?
C2 C3 C7 C8 -179.7(3) . . . . ?
C3 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C8 C9 C10 C11 -178.8(4) . . . . ?
C8 C9 C10 C4 0.8(5) . . . . ?
C3 C4 C10 C9 -0.8(4) . . . . ?
C5 C4 C10 C9 179.8(3) . . . . ?
C3 C4 C10 C11 178.8(3) . . . . ?
C5 C4 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 179.7(3) . . . . ?
C4 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C6 C5 C13 C14 -0.3(3) . . . . ?
C4 C5 C13 C14 -179.8(2) . . . . ?
C6 C5 C13 C12 -179.6(2) . . . . ?
C4 C5 C13 C12 0.9(3) . . . . ?
C11 C12 C13 C14 179.4(3) . . . . ?
C11 C12 C13 C5 -1.4(4) . . . . ?
C5 C13 C14 C15 1.2(4) . . . . ?
C12 C13 C14 C15 -179.5(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C6 -1.1(4) . . . . ?
C14 C15 C16 C17 179.7(2) . . . . ?
C5 C6 C16 C15 1.9(3) . . . . ?
C1 C6 C16 C15 -178.0(2) . . . . ?
C5 C6 C16 C17 -178.9(2) . . . . ?
C1 C6 C16 C17 1.2(4) . . . . ?
C15 C16 C17 N1 -35.5(3) . . . . ?
C6 C16 C17 N1 145.3(2) . . . . ?
C15 C16 C17 C18 78.0(3) . . . . ?
C6 C16 C17 C18 -101.2(3) . . . . ?
N1 C17 C18 C19 1.2(2) . . . . ?
C16 C17 C18 C19 -118.1(2) . . . . ?
C17 C18 C19 N2 -0.1(3) . . . . ?
C17 C18 C19 C22 -177.4(2) . . . . ?
N2 C19 C22 C27 177.9(3) . . . . ?
C18 C19 C22 C27 -4.9(4) . . . . ?
N2 C19 C22 C23 -5.0(4) . . . . ?
C18 C19 C22 C23 172.2(3) . . . . ?
C27 C22 C23 C24 0.6(5) . . . . ?
C19 C22 C23 C24 -176.5(3) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C23 C24 C25 C26 -0.8(7) . . . . ?
C24 C25 C26 C27 1.0(7) . . . . ?
C25 C26 C27 C22 -0.4(7) . . . . ?
C23 C22 C27 C26 -0.4(5) . . . . ?
C19 C22 C27 C26 176.7(4) . . . . ?
O1 C20 N1 N2 173.8(2) . . . . ?
C21 C20 N1 N2 -8.2(3) . . . . ?
O1 C20 N1 C17 -2.9(4) . . . . ?
C21 C20 N1 C17 175.2(2) . . . . ?
C16 C17 N1 C20 -63.1(3) . . . . ?
C18 C17 N1 C20 174.9(2) . . . . ?
C16 C17 N1 N2 120.0(2) . . . . ?
C18 C17 N1 N2 -2.0(3) . . . . ?
C22 C19 N2 N1 176.3(2) . . . . ?
C18 C19 N2 N1 -1.1(3) . . . . ?
C20 N1 N2 C19 -174.9(2) . . . . ?
C17 N1 N2 C19 2.0(3) . . . . ?
C28 C29 C30 O3 3.3(5) . . . . ?
C28 C29 C30 O2 -177.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.82 1.80 2.613(3) 169.9 .

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fq3_a
_database_code_depnum_ccdc_archive 'CCDC 1580855'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;         
1-acetyl-3-(phenyl)-5-(1-pyrenyl) pyrazoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C108 H80 N8 O4'
_chemical_formula_weight         1553.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3054(9)
_cell_length_b                   28.633(3)
_cell_length_c                   15.6531(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.437(3)
_cell_angle_gamma                90
_cell_volume                     4056.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      22.76

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46800
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9272
_reflns_number_gt                4464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+0.4881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9272
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5497(2) 0.21347(8) 0.65229(13) 0.0623(5) Uani 1 1 d . . . . .
H1 H 0.5041 0.2380 0.6748 0.075 Uiso 1 1 calc R U . . .
C2 C 0.5594(2) 0.17195(8) 0.69173(15) 0.0716(6) Uani 1 1 d . . . . .
H2 H 0.5190 0.1682 0.7403 0.086 Uiso 1 1 calc R U . . .
C3 C 0.6299(2) 0.13329(8) 0.66158(16) 0.0698(6) Uani 1 1 d . . . . .
C4 C 0.6908(2) 0.13954(7) 0.58779(14) 0.0573(5) Uani 1 1 d . . . . .
C5 C 0.67877(19) 0.18360(7) 0.54465(12) 0.0502(5) Uani 1 1 d . . . . .
C6 C 0.60753(19) 0.22150(7) 0.57621(12) 0.0496(5) Uani 1 1 d . . . . .
C7 C 0.6428(3) 0.08968(10) 0.7017(2) 0.0981(9) Uani 1 1 d . . . . .
H7 H 0.6027 0.0849 0.7501 0.118 Uiso 1 1 calc R U . . .
C8 C 0.7136(3) 0.05362(10) 0.6711(2) 0.1146(11) Uani 1 1 d . . . . .
H8 H 0.7204 0.0247 0.6989 0.138 Uiso 1 1 calc R U . . .
C9 C 0.7746(3) 0.05946(9) 0.6001(2) 0.0943(8) Uani 1 1 d . . . . .
H9 H 0.8232 0.0346 0.5808 0.113 Uiso 1 1 calc R U . . .
C10 C 0.7646(2) 0.10209(8) 0.55675(16) 0.0681(6) Uani 1 1 d . . . . .
C11 C 0.8250(2) 0.10956(9) 0.48247(17) 0.0742(6) Uani 1 1 d . . . . .
H11 H 0.8733 0.0851 0.4617 0.089 Uiso 1 1 calc R U . . .
C12 C 0.8142(2) 0.15091(9) 0.44167(15) 0.0684(6) Uani 1 1 d . . . . .
H12 H 0.8554 0.1546 0.3933 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7404(2) 0.18958(7) 0.47093(13) 0.0551(5) Uani 1 1 d . . . . .
C14 C 0.7278(2) 0.23275(8) 0.42954(14) 0.0627(6) Uani 1 1 d . . . . .
H14 H 0.7665 0.2370 0.3804 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6583(2) 0.26930(7) 0.46060(13) 0.0597(5) Uani 1 1 d . . . . .
H15 H 0.6515 0.2980 0.4319 0.072 Uiso 1 1 calc R U . . .
C16 C 0.59825(19) 0.26469(7) 0.53324(13) 0.0513(5) Uani 1 1 d . . . . .
C17 C 0.5343(2) 0.30618(7) 0.57120(13) 0.0579(5) Uani 1 1 d . . . . .
H17 H 0.4450 0.2968 0.5899 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6464(2) 0.32741(7) 0.64859(13) 0.0607(5) Uani 1 1 d . . . . .
H18A H 0.6060 0.3297 0.7003 0.073 Uiso 1 1 calc R U . . .
H18B H 0.7366 0.3092 0.6627 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6732(2) 0.37449(7) 0.61521(14) 0.0541(5) Uani 1 1 d . . . . .
C20 C 0.3872(3) 0.34693(10) 0.44005(16) 0.0798(7) Uani 1 1 d . . . . .
C21 C 0.3639(3) 0.39110(10) 0.38846(17) 0.1078(10) Uani 1 1 d . . . . .
H21A H 0.2876 0.3866 0.3361 0.162 Uiso 1 1 calc R U . . .
H21B H 0.4541 0.3998 0.3728 0.162 Uiso 1 1 calc R U . . .
H21C H 0.3351 0.4154 0.4232 0.162 Uiso 1 1 calc R U . . .
C22 C 0.7791(2) 0.40755(8) 0.66428(14) 0.0632(6) Uani 1 1 d . . . . .
C23 C 0.7660(3) 0.45513(9) 0.64764(18) 0.0937(8) Uani 1 1 d . . . . .
H23 H 0.6890 0.4664 0.6035 0.112 Uiso 1 1 calc R U . . .
C24 C 0.8658(6) 0.48552(13) 0.6958(3) 0.1398(15) Uani 1 1 d . . . . .
H24 H 0.8561 0.5174 0.6847 0.168 Uiso 1 1 calc R U . . .
C25 C 0.9804(5) 0.4692(2) 0.7607(3) 0.152(2) Uani 1 1 d . . . . .
H25 H 1.0483 0.4901 0.7931 0.183 Uiso 1 1 calc R U . . .
C26 C 0.9949(4) 0.42257(17) 0.7778(2) 0.1257(13) Uani 1 1 d . . . . .
H26 H 1.0726 0.4116 0.8218 0.151 Uiso 1 1 calc R U . . .
C27 C 0.8945(3) 0.39173(10) 0.72976(15) 0.0830(7) Uani 1 1 d . . . . .
H27 H 0.9046 0.3599 0.7416 0.100 Uiso 1 1 calc R U . . .
C28 C 0.1571(2) 0.32682(7) 0.64019(13) 0.0563(5) Uani 1 1 d . . . . .
C29 C 0.0557(3) 0.34037(9) 0.56082(13) 0.0715(6) Uani 1 1 d . . . . .
H29 H -0.0128 0.3188 0.5314 0.086 Uiso 1 1 calc R U . . .
C30 C 0.0571(3) 0.38365(10) 0.52765(16) 0.0910(8) Uani 1 1 d . . . . .
H30 H -0.0121 0.3914 0.4765 0.109 Uiso 1 1 calc R U . . .
C31 C 0.1612(4) 0.41805(9) 0.56836(18) 0.0900(8) Uani 1 1 d . . . . .
C32 C 0.2640(3) 0.40605(9) 0.64681(16) 0.0754(7) Uani 1 1 d . . . . .
C33 C 0.2604(2) 0.36081(8) 0.68317(14) 0.0617(6) Uani 1 1 d . . . . .
C34 C 0.1680(5) 0.46274(12) 0.5334(2) 0.1270(12) Uani 1 1 d . . . . .
H34 H 0.1020 0.4710 0.4813 0.152 Uiso 1 1 calc R U . . .
C35 C 0.2712(6) 0.49465(13) 0.5750(3) 0.1483(17) Uani 1 1 d . . . . .
H35 H 0.2736 0.5244 0.5514 0.178 Uiso 1 1 calc R U . . .
C36 C 0.3703(5) 0.48289(13) 0.6512(3) 0.1331(14) Uani 1 1 d . . . . .
H36 H 0.4398 0.5049 0.6780 0.160 Uiso 1 1 calc R U . . .
C37 C 0.3704(4) 0.43923(10) 0.6895(2) 0.0936(9) Uani 1 1 d . . . . .
C38 C 0.4695(4) 0.42619(13) 0.7690(3) 0.1073(10) Uani 1 1 d . . . . .
H38 H 0.5392 0.4477 0.7975 0.129 Uiso 1 1 calc R U . . .
C39 C 0.4654(3) 0.38443(12) 0.8036(2) 0.0975(9) Uani 1 1 d . . . . .
H39 H 0.5327 0.3773 0.8558 0.117 Uiso 1 1 calc R U . . .
C40 C 0.3611(2) 0.34973(9) 0.76336(16) 0.0717(6) Uani 1 1 d . . . . .
C41 C 0.3564(2) 0.30581(10) 0.79767(16) 0.0785(7) Uani 1 1 d . . . . .
H41 H 0.4214 0.2982 0.8505 0.094 Uiso 1 1 calc R U . . .
C42 C 0.2578(2) 0.27279(8) 0.75575(14) 0.0695(6) Uani 1 1 d . . . . .
H42 H 0.2582 0.2433 0.7807 0.083 Uiso 1 1 calc R U . . .
C43 C 0.1581(2) 0.28236(8) 0.67741(12) 0.0562(5) Uani 1 1 d . . . . .
C44 C 0.0566(2) 0.24422(7) 0.63200(13) 0.0608(5) Uani 1 1 d . . . . .
H44 H -0.0360 0.2579 0.5983 0.073 Uiso 1 1 calc R U . . .
C45 C 0.1257(2) 0.21321(8) 0.57180(13) 0.0678(6) Uani 1 1 d . . . . .
H45A H 0.0632 0.2118 0.5129 0.081 Uiso 1 1 calc R U . . .
H45B H 0.2226 0.2246 0.5688 0.081 Uiso 1 1 calc R U . . .
C46 C 0.1360(2) 0.16651(8) 0.61573(14) 0.0623(6) Uani 1 1 d . . . . .
C47 C -0.0468(2) 0.21885(9) 0.75821(13) 0.0609(5) Uani 1 1 d . . . . .
C48 C -0.0579(2) 0.18005(8) 0.81953(14) 0.0758(7) Uani 1 1 d . . . . .
H48A H 0.0345 0.1767 0.8618 0.114 Uiso 1 1 calc R U . . .
H48B H -0.0807 0.1515 0.7870 0.114 Uiso 1 1 calc R U . . .
H48C H -0.1347 0.1869 0.8494 0.114 Uiso 1 1 calc R U . . .
C49 C 0.2002(2) 0.12395(9) 0.58795(15) 0.0708(6) Uani 1 1 d . . . . .
C50 C 0.1912(3) 0.08167(10) 0.62965(18) 0.0890(8) Uani 1 1 d . . . . .
H50 H 0.1423 0.0803 0.6751 0.107 Uiso 1 1 calc R U . . .
C51 C 0.2527(3) 0.04209(11) 0.6051(2) 0.1148(10) Uani 1 1 d . . . . .
H51 H 0.2465 0.0142 0.6344 0.138 Uiso 1 1 calc R U . . .
C52 C 0.3231(4) 0.04320(16) 0.5382(3) 0.1289(13) Uani 1 1 d . . . . .
H52 H 0.3650 0.0161 0.5218 0.155 Uiso 1 1 calc R U . . .
C53 C 0.3321(4) 0.08395(16) 0.4953(2) 0.1200(12) Uani 1 1 d . . . . .
H53 H 0.3796 0.0845 0.4492 0.144 Uiso 1 1 calc R U . . .
C54 C 0.2710(3) 0.12503(11) 0.51934(17) 0.0960(8) Uani 1 1 d . . . . .
H54 H 0.2777 0.1528 0.4896 0.115 Uiso 1 1 calc R U . . .
N1 N 0.50201(19) 0.34607(6) 0.51166(11) 0.0652(5) Uani 1 1 d . . . . .
N2 N 0.5915(2) 0.38458(6) 0.53984(12) 0.0632(5) Uani 1 1 d . . . . .
N3 N 0.02513(18) 0.20950(6) 0.69420(11) 0.0609(4) Uani 1 1 d . . . . .
N4 N 0.07935(18) 0.16532(6) 0.68314(11) 0.0624(5) Uani 1 1 d . . . . .
O1 O 0.3116(2) 0.31206(7) 0.42074(13) 0.1048(6) Uani 1 1 d . . . . .
O2 O -0.09517(17) 0.25813(6) 0.76368(10) 0.0765(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.333(3) . ?
C1 C6 1.435(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.422(3) . ?
C2 H2 0.9300 . ?
C3 C7 1.390(3) . ?
C3 C4 1.411(3) . ?
C4 C10 1.419(3) . ?
C4 C5 1.423(3) . ?
C5 C13 1.414(3) . ?
C5 C6 1.419(2) . ?
C6 C16 1.401(3) . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(3) . ?
C11 C12 1.338(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.433(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(3) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.511(3) . ?
C17 N1 1.461(3) . ?
C17 C18 1.529(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.488(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N2 1.279(2) . ?
C19 C22 1.451(3) . ?
C20 O1 1.218(3) . ?
C20 N1 1.357(3) . ?
C20 C21 1.489(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.377(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.365(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C43 1.399(3) . ?
C28 C33 1.423(3) . ?
C28 C29 1.428(3) . ?
C29 C30 1.345(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.424(4) . ?
C30 H30 0.9300 . ?
C31 C34 1.399(4) . ?
C31 C32 1.413(4) . ?
C32 C33 1.418(3) . ?
C32 C37 1.422(4) . ?
C33 C40 1.417(3) . ?
C34 C35 1.375(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.386(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.416(4) . ?
C38 C39 1.316(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.429(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.372(3) . ?
C41 C42 1.373(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.382(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.509(3) . ?
C44 N3 1.468(2) . ?
C44 C45 1.540(3) . ?
C44 H44 0.9800 . ?
C45 C46 1.497(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 N4 1.285(2) . ?
C46 C49 1.467(3) . ?
C47 O2 1.222(2) . ?
C47 N3 1.355(2) . ?
C47 C48 1.487(3) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C54 1.384(3) . ?
C49 C50 1.387(3) . ?
C50 C51 1.364(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.359(5) . ?
C51 H51 0.9300 . ?
C52 C53 1.359(5) . ?
C52 H52 0.9300 . ?
C53 C54 1.396(4) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
N1 N2 1.390(2) . ?
N3 N4 1.387(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.0(2) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C7 C3 C4 118.3(2) . . ?
C7 C3 C2 123.2(2) . . ?
C4 C3 C2 118.5(2) . . ?
C3 C4 C10 120.2(2) . . ?
C3 C4 C5 119.90(19) . . ?
C10 C4 C5 119.90(19) . . ?
C13 C5 C6 120.18(18) . . ?
C13 C5 C4 119.52(18) . . ?
C6 C5 C4 120.29(17) . . ?
C16 C6 C5 119.32(17) . . ?
C16 C6 C1 123.15(18) . . ?
C5 C6 C1 117.52(18) . . ?
C8 C7 C3 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C3 C7 H7 119.4 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C4 118.6(2) . . ?
C9 C10 C11 122.6(2) . . ?
C4 C10 C11 118.8(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C5 118.84(18) . . ?
C14 C13 C12 122.29(19) . . ?
C5 C13 C12 118.9(2) . . ?
C15 C14 C13 120.55(19) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.97(19) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C6 119.13(17) . . ?
C15 C16 C17 121.26(18) . . ?
C6 C16 C17 119.43(17) . . ?
N1 C17 C16 113.91(16) . . ?
N1 C17 C18 101.30(15) . . ?
C16 C17 C18 111.45(16) . . ?
N1 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
C18 C17 H17 110.0 . . ?
C19 C18 C17 102.78(17) . . ?
C19 C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
C19 C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
N2 C19 C22 121.73(19) . . ?
N2 C19 C18 114.60(18) . . ?
C22 C19 C18 123.64(19) . . ?
O1 C20 N1 119.3(2) . . ?
O1 C20 C21 124.0(2) . . ?
N1 C20 C21 116.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 118.8(2) . . ?
C27 C22 C19 119.7(2) . . ?
C23 C22 C19 121.5(2) . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C43 C28 C33 119.15(19) . . ?
C43 C28 C29 123.3(2) . . ?
C33 C28 C29 117.6(2) . . ?
C30 C29 C28 121.5(2) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 122.1(2) . . ?
C29 C30 H30 119.0 . . ?
C31 C30 H30 119.0 . . ?
C34 C31 C32 118.7(3) . . ?
C34 C31 C30 123.1(3) . . ?
C32 C31 C30 118.3(2) . . ?
C31 C32 C33 119.8(2) . . ?
C31 C32 C37 120.2(3) . . ?
C33 C32 C37 120.0(3) . . ?
C40 C33 C32 119.2(2) . . ?
C40 C33 C28 120.0(2) . . ?
C32 C33 C28 120.7(2) . . ?
C35 C34 C31 120.8(4) . . ?
C35 C34 H34 119.6 . . ?
C31 C34 H34 119.6 . . ?
C36 C35 C34 120.3(4) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 122.1(4) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C36 C37 C38 123.6(4) . . ?
C36 C37 C32 118.0(4) . . ?
C38 C37 C32 118.5(3) . . ?
C39 C38 C37 121.7(3) . . ?
C39 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C38 C39 C40 122.1(3) . . ?
C38 C39 H39 118.9 . . ?
C40 C39 H39 118.9 . . ?
C41 C40 C33 118.5(2) . . ?
C41 C40 C39 123.0(3) . . ?
C33 C40 C39 118.4(3) . . ?
C40 C41 C42 121.5(2) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C41 C42 C43 121.6(2) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C42 C43 C28 119.2(2) . . ?
C42 C43 C44 119.5(2) . . ?
C28 C43 C44 121.28(17) . . ?
N3 C44 C43 112.15(16) . . ?
N3 C44 C45 101.03(16) . . ?
C43 C44 C45 113.60(16) . . ?
N3 C44 H44 109.9 . . ?
C43 C44 H44 109.9 . . ?
C45 C44 H44 109.9 . . ?
C46 C45 C44 103.01(16) . . ?
C46 C45 H45A 111.2 . . ?
C44 C45 H45A 111.2 . . ?
C46 C45 H45B 111.2 . . ?
C44 C45 H45B 111.2 . . ?
H45A C45 H45B 109.1 . . ?
N4 C46 C49 119.7(2) . . ?
N4 C46 C45 113.98(19) . . ?
C49 C46 C45 126.36(19) . . ?
O2 C47 N3 119.1(2) . . ?
O2 C47 C48 124.10(19) . . ?
N3 C47 C48 116.7(2) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C54 C49 C50 118.4(2) . . ?
C54 C49 C46 120.8(3) . . ?
C50 C49 C46 120.8(2) . . ?
C51 C50 C49 121.1(3) . . ?
C51 C50 H50 119.4 . . ?
C49 C50 H50 119.4 . . ?
C52 C51 C50 120.4(4) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C53 C52 C51 119.8(3) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 121.0(3) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C49 C54 C53 119.2(3) . . ?
C49 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?
C20 N1 N2 123.1(2) . . ?
C20 N1 C17 123.1(2) . . ?
N2 N1 C17 113.48(16) . . ?
C19 N2 N1 107.30(16) . . ?
C47 N3 N4 121.93(18) . . ?
C47 N3 C44 124.44(18) . . ?
N4 N3 C44 113.61(15) . . ?
C46 N4 N3 107.99(18) . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035

