# 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_SQ7+resorcinol
_audit_block_doi                 10.5517/cc139rx2
_database_code_depnum_ccdc_archive 'CCDC 1022284'
_audit_update_record             
;
2014-09-01 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

#=============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            'C12 H22 N4 O2, C6 H6 O2'
_chemical_formula_moiety         'C12 H22 N4 O2, C6 H6 O2'
_chemical_formula_structural     'C12 H22 N4 O2, C6 H6 O2'
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C18 H28 N4 O4'
_chemical_formula_weight         364
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and 
# natural products

loop_
_atom_type_symbol
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
h 0.49300 10.51090 0.32291 26.12570 0.14019 3.14236 0.04081 57.79970 0.00304
0.00000 0.00000
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
c 2.31000 20.84390 1.02000 10.20750 1.58860 0.56870 0.86500 51.65120 0.21560
0.01700 0.00900
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
o 3.04850 13.27710 2.28680 5.70110 1.54630 0.32390 0.86700 32.90890 0.25080
0.04700 0.03200
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
n 12.21260 0.00570 3.13220 9.89330 2.01250 28.99750 1.16630 0.58260 -11.52900
0.02900 0.01800
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5

#=============================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'

loop_
_symmetry_equiv_pos_as_xyz #<--must include 'x,y,z'
x,y,z
-y,x+1/2,z+1/2
-x+1/2,-y+1/2,z
y+1/2,-x,z+1/2
-x,-y,-z
y,-x+1/2,-z+1/2
x+1/2,y+1/2,-z
-y+1/2,x,-z+1/2

_cell_length_a                   25.43120(12)
_cell_length_b                   25.43120(12)
_cell_length_c                   6.06772(3)
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_volume                     3924.27(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293
_cell_special_details            
; ?
;
# The next three fields give the specimen dimensions in mm.  The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              ? # perpendicular to 
# equatorial plane
_pd_spec_size_equat              ? # parallel to 
# scattering vector
# in transmission
_pd_spec_size_thick              ? # parallel to 
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the 
# container.
; ?
;
_pd_spec_mount_mode              ? # options are 'reflection'
# or 'transmission'
_pd_spec_shape                   ? # options are 'cylinder' 
# 'flat_sheet' or 'irregular'
_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min.  The pressure at which the sample was 
# prepared is in kPa.  The temperature of preparation is in K.        

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

# The next four fields are normally only needed for transmission experiments.

_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

#=============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_source_target            Cu

_diffrn_radiation_monochromator  'elliptic x-ray mirror'
_diffrn_measurement_device_type  "PANalytical X'Pert PRO MPD"
_diffrn_radiation_wavelength     1.5418
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ? # Not in version 2.0.1
_diffrn_detector                 ?
_diffrn_detector_type            ? # make or model of detector
_pd_meas_scan_method             ? # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
;  ?
;

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5230
_pd_meas_2theta_range_min        2.00700
_pd_meas_2theta_range_max        69.98400
_pd_meas_2theta_range_inc        0.013002

#=============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_proc_ls_profile_function     ?
_pd_proc_ls_background_function  ?
_pd_proc_ls_pref_orient_corr     
; ?
;

#  The following profile R-factors are NOT CORRECTED for background
#  The sum is extended to all non-excluded points.
#  These are the current CIF standard

_pd_proc_ls_prof_R_factor        2.8898
_pd_proc_ls_prof_wR_factor       4.0147
_pd_proc_ls_prof_wR_expected     1.3011

#  The following profile R-factors are CORRECTED for background
#  The sum is extended to all non-excluded points.
#  These items are not in the current CIF standard, but are defined above

_pd_proc_ls_prof_cR_factor       8.4285
_pd_proc_ls_prof_cwR_factor      8.5302
_pd_proc_ls_prof_cwR_expected    2.7645

#  The following items are not in the CIF standard, but are defined above

_pd_proc_ls_prof_chi2            9.5212
_pd_proc_ls_prof_echi2           9.5608

#  Items related to LS refinement

_refine_ls_R_I_factor            2.7267
_refine_ls_number_reflns         2060
_refine_ls_number_parameters     126
_refine_ls_number_restraints     146
_refine_ls_goodness_of_fit_all   9.52

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        2.0295
_pd_proc_2theta_range_max        70.0065
_pd_proc_2theta_range_inc        0.013002
_pd_proc_wavelength              1.541840

_pd_block_diffractogram_id       ? # The id used for the block containing
# the powder pattern profile (section 11)

# Give appropriate details in the next two text fields.

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

# The following items are used to identify the programs used.

_computing_data_collection       ?
_computing_structure_solution    ?
_computing_structure_refinement  FULLPROF
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type # Not in version 2.0.1
_atom_site_type_symbol
H1 0.50384 0.24728 0.55049 0.180(15) 1.00000 Uiso H
C2 0.50446 0.23553 0.38052 0.0320(19) 1.00000 Uiso C
C3 0.50668 0.19701 -0.05126 0.0320(19) 1.00000 Uiso C
C4 0.54473 0.20230 0.31185 0.0320(19) 1.00000 Uiso C
C5 0.46529 0.24931 0.23106 0.0320(19) 1.00000 Uiso C
C6 0.46610 0.23032 0.01596 0.0320(19) 1.00000 Uiso C
C7 0.54624 0.18285 0.09699 0.0320(19) 1.00000 Uiso C
H8 0.43801 0.24480 -0.10665 0.180(15) 1.00000 Uiso H
H9 0.57450 0.15257 0.05185 0.180(15) 1.00000 Uiso H
H10 0.50570 0.17983 -0.21593 0.180(15) 1.00000 Uiso H
O11 0.5810(2) 0.1884(3) 0.4616(11) 0.039(2) 1.00000 Uiso O
H12 0.60520 0.16340 0.39690 0.180(15) 1.00000 Uiso H
O13 0.4260(2) 0.2835(3) 0.2865(11) 0.039(2) 1.00000 Uiso O
H14 0.40150 0.28710 0.16770 0.180(15) 1.00000 Uiso H
O15 0.9309(3) -0.0368(3) 1.3506(11) 0.039(2) 1.00000 Uiso O
N16 0.8606(3) -0.1619(3) 0.9723(12) 0.036(3) 1.00000 Uiso N
N17 0.9285(4) -0.0357(2) 0.8218(10) 0.036(3) 1.00000 Uiso N
H18 0.93191 -0.02810 0.67141 0.180(15) 1.00000 Uiso H
C19 0.8708(3) -0.1632(3) 1.2124(12) 0.0320(19) 1.00000 Uiso C
H20 0.87058 -0.12739 1.26775 0.180(15) 1.00000 Uiso H
H21 0.84860 -0.18578 1.28800 0.180(15) 1.00000 Uiso H
H22 0.90759 -0.17623 1.23196 0.180(15) 1.00000 Uiso H
C23 0.8054(3) -0.1804(3) 0.9446(11) 0.0320(19) 1.00000 Uiso C
H24 0.80038 -0.19978 0.81050 0.180(15) 1.00000 Uiso H
H25 0.79316 -0.20014 1.06840 0.180(15) 1.00000 Uiso H
H26 0.78244 -0.14830 0.93380 0.180(15) 1.00000 Uiso H
C27 0.8672(3) -0.1078(3) 0.8774(12) 0.0320(19) 1.00000 Uiso C
H28 0.85619 -0.10996 0.72191 0.180(15) 1.00000 Uiso H
H29 0.84459 -0.08435 0.95121 0.180(15) 1.00000 Uiso H
C30 0.9241(3) -0.0922(3) 0.8733(12) 0.0320(19) 1.00000 Uiso C
H31 0.94468 -0.11283 0.77840 0.180(15) 1.00000 Uiso H
H32 0.93729 -0.09718 1.02568 0.180(15) 1.00000 Uiso H
C33 0.93591 -0.00019 0.97289 0.0320(19) 1.00000 Uiso C
C34 0.93637 -0.00116 1.21719 0.0320(19) 1.00000 Uiso C
O35 0.9474(3) 0.0925(3) 1.3429(12) 0.039(2) 1.00000 Uiso O
N36 0.8638(3) 0.1726(4) 0.8736(11) 0.036(3) 1.00000 Uiso N
N37 0.9442(5) 0.0906(3) 0.8065(11) 0.036(3) 1.00000 Uiso N
H38 0.93820 0.08260 0.65140 0.180(15) 1.00000 Uiso H
C39 0.8652(3) 0.1904(3) 1.1085(11) 0.0320(19) 1.00000 Uiso C
H40 0.86779 0.22795 1.12347 0.180(15) 1.00000 Uiso H
H41 0.83569 0.17806 1.19032 0.180(15) 1.00000 Uiso H
H42 0.89648 0.17760 1.19363 0.180(15) 1.00000 Uiso H
C43 0.8220(3) 0.2017(3) 0.7638(11) 0.0320(19) 1.00000 Uiso C
H44 0.79285 0.17906 0.76990 0.180(15) 1.00000 Uiso H
H45 0.83398 0.20568 0.61003 0.180(15) 1.00000 Uiso H
H46 0.81650 0.23386 0.83626 0.180(15) 1.00000 Uiso H
C47 0.9158(2) 0.1804(3) 0.7746(12) 0.0320(19) 1.00000 Uiso C
H48 0.91326 0.17721 0.61601 0.180(15) 1.00000 Uiso H
H49 0.92915 0.21726 0.80005 0.180(15) 1.00000 Uiso H
C50 0.9595(3) 0.1445(3) 0.8494(12) 0.0320(19) 1.00000 Uiso C
H51 0.96448 0.15062 1.00709 0.180(15) 1.00000 Uiso H
H52 0.99212 0.15428 0.77766 0.180(15) 1.00000 Uiso H
C53 0.94142 0.05517 0.96988 0.0320(19) 1.00000 Uiso C
C54 0.94418 0.05723 1.21412 0.0320(19) 1.00000 Uiso C

# Note: if the displacement parameters were refined anisotropically
# the U matrices should be given as for single-crystal studies.

#=============================================================================

# 10. DISTANCES AND ANGLES / MOLECULAR GEOMETRY 

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

? ? ? ? ? ?
H1 C2 ? ? 1.0739 ?
C2 C4 ? ? 1.3916 ?
C2 C5 ? ? 1.3920 ?
C3 C6 ? ? 1.3961 ?
C3 C7 ? ? 1.3968 ?
C3 H10 ? ? 1.0908 ?
C4 C7 ? ? 1.3949 ?
C4 O11 ? ? 1.342(6) ?
C5 C6 ? ? 1.3918 ?
C5 O13 ? ? 1.367(6) ?
C6 H8 ? ? 1.0952 ?
C7 H9 ? ? 1.0884 ?
O11 H12 ? ? 0.968(7) ?
O13 H14 ? ? 0.957(6) ?
O15 C34 ? ? 1.223(7) ?
N16 C19 ? ? 1.48(1) ?
N16 C23 ? ? 1.49(1) ?
N16 C27 ? ? 1.50(1) ?
N17 H18 ? ? 0.937(6) ?
N17 C30 ? ? 1.475(9) ?
N17 C33 ? ? 1.301(6) ?
C19 H20 ? ? 0.971(8) ?
C19 H21 ? ? 0.927(8) ?
C19 H22 ? ? 1.000(8) ?
C23 H24 ? ? 0.960(7) ?
C23 H25 ? ? 0.956(7) ?
C23 H26 ? ? 1.006(8) ?
C27 H28 ? ? 0.986(7) ?
C27 H29 ? ? 0.942(8) ?
C27 C30 ? ? 1.50(1) ?
C30 H31 ? ? 0.938(8) ?
C30 H32 ? ? 0.992(7) ?
C33 C34 ? ? 1.4826 ?
C33 C53 ? ? 1.4149 ?
C34 C54 ? ? 1.4983 ?
O35 C54 ? ? 1.192(7) ?
N36 C39 ? ? 1.50(1) ?
N36 C43 ? ? 1.46(1) ?
N36 C47 ? ? 1.466(9) ?
N37 H38 ? ? 0.975(7) ?
N37 C50 ? ? 1.45(1) ?
N37 C53 ? ? 1.341(7) ?
C39 H40 ? ? 0.962(8) ?
C39 H41 ? ? 0.953(7) ?
C39 H42 ? ? 1.003(7) ?
C43 H44 ? ? 0.939(8) ?
C43 H45 ? ? 0.987(7) ?
C43 H46 ? ? 0.939(7) ?
C47 H48 ? ? 0.968(7) ?
C47 H49 ? ? 1.009(7) ?
C47 C50 ? ? 1.51(1) ?
C50 H51 ? ? 0.978(7) ?
C50 H52 ? ? 0.969(8) ?
C53 C54 ? ? 1.4846 ?


loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

? ? ? ? ? ? ? ?
H1 C2 C4 ? ? ? 117.86 ?
H1 C2 C5 ? ? ? 123.03 ?
C4 C2 C5 ? ? ? 118.98 ?
C6 C3 C7 ? ? ? 120.05 ?
C6 C3 H10 ? ? ? 119.59 ?
C7 C3 H10 ? ? ? 120.21 ?
C2 C4 C7 ? ? ? 121.03 ?
C2 C4 O11 ? ? ? 117.6(3) ?
C7 C4 O11 ? ? ? 121.4(3) ?
C2 C5 C6 ? ? ? 120.86 ?
C2 C5 O13 ? ? ? 121.5(3) ?
C6 C5 O13 ? ? ? 117.5(3) ?
C3 C6 C5 ? ? ? 119.70 ?
C3 C6 H8 ? ? ? 119.19 ?
C5 C6 H8 ? ? ? 120.71 ?
C3 C7 C4 ? ? ? 119.38 ?
C3 C7 H9 ? ? ? 119.73 ?
C4 C7 H9 ? ? ? 120.28 ?
C4 O11 H12 ? ? ? 109.6(5) ?
C5 O13 H14 ? ? ? 110.6(5) ?
C19 N16 C23 ? ? ? 105.6(6) ?
C19 N16 C27 ? ? ? 112.2(6) ?
C23 N16 C27 ? ? ? 110.6(6) ?
H18 N17 C30 ? ? ? 114.5(7) ?
H18 N17 C33 ? ? ? 122.0(7) ?
C30 N17 C33 ? ? ? 122.6(6) ?
N16 C19 H20 ? ? ? 108.6(7) ?
N16 C19 H21 ? ? ? 113.2(7) ?
N16 C19 H22 ? ? ? 106.8(7) ?
H20 C19 H21 ? ? ? 114.0(8) ?
H20 C19 H22 ? ? ? 106.0(7) ?
H21 C19 H22 ? ? ? 107.8(7) ?
N16 C23 H24 ? ? ? 112.5(7) ?
N16 C23 H25 ? ? ? 112.6(7) ?
N16 C23 H26 ? ? ? 107.3(6) ?
H24 C23 H25 ? ? ? 110.7(7) ?
H24 C23 H26 ? ? ? 106.5(7) ?
H25 C23 H26 ? ? ? 106.8(7) ?
N16 C27 H28 ? ? ? 106.5(7) ?
N16 C27 H29 ? ? ? 109.3(7) ?
N16 C27 C30 ? ? ? 110.9(6) ?
H28 C27 H29 ? ? ? 108.5(7) ?
H28 C27 C30 ? ? ? 105.8(7) ?
H29 C27 C30 ? ? ? 115.4(7) ?
N17 C30 C27 ? ? ? 109.5(6) ?
N17 C30 H31 ? ? ? 111.9(7) ?
N17 C30 H32 ? ? ? 107.2(7) ?
C27 C30 H31 ? ? ? 113.6(7) ?
C27 C30 H32 ? ? ? 106.1(6) ?
H31 C30 H32 ? ? ? 108.2(7) ?
N17 C33 C34 ? ? ? 134.0(3) ?
N17 C33 C53 ? ? ? 134.1(3) ?
C34 C33 C53 ? ? ? 91.64 ?
O15 C34 C33 ? ? ? 132.3(3) ?
O15 C34 C54 ? ? ? 139.3(3) ?
C33 C34 C54 ? ? ? 88.40 ?
C39 N36 C43 ? ? ? 107.4(6) ?
C39 N36 C47 ? ? ? 109.1(6) ?
C43 N36 C47 ? ? ? 113.7(7) ?
H38 N37 C50 ? ? ? 114.4(8) ?
H38 N37 C53 ? ? ? 124.4(8) ?
C50 N37 C53 ? ? ? 121.1(7) ?
N36 C39 H40 ? ? ? 113.1(7) ?
N36 C39 H41 ? ? ? 112.2(7) ?
N36 C39 H42 ? ? ? 114.3(7) ?
H40 C39 H41 ? ? ? 109.4(7) ?
H40 C39 H42 ? ? ? 102.7(7) ?
H41 C39 H42 ? ? ? 104.4(7) ?
N36 C43 H44 ? ? ? 104.3(7) ?
N36 C43 H45 ? ? ? 105.0(7) ?
N36 C43 H46 ? ? ? 109.7(7) ?
H44 C43 H45 ? ? ? 110.1(7) ?
H44 C43 H46 ? ? ? 113.4(7) ?
H45 C43 H46 ? ? ? 113.5(7) ?
N36 C47 H48 ? ? ? 109.6(6) ?
N36 C47 H49 ? ? ? 111.5(6) ?
N36 C47 C50 ? ? ? 117.4(6) ?
H48 C47 H49 ? ? ? 104.6(6) ?
H48 C47 C50 ? ? ? 107.3(6) ?
H49 C47 C50 ? ? ? 105.6(6) ?
N37 C50 C47 ? ? ? 108.7(6) ?
N37 C50 H51 ? ? ? 111.2(7) ?
N37 C50 H52 ? ? ? 113.1(7) ?
C47 C50 H51 ? ? ? 107.1(6) ?
C47 C50 H52 ? ? ? 109.9(7) ?
H51 C50 H52 ? ? ? 106.7(7) ?
C33 C53 N37 ? ? ? 133.1(4) ?
C33 C53 C54 ? ? ? 91.54 ?
N37 C53 C54 ? ? ? 135.4(4) ?
C34 C54 O35 ? ? ? 138.3(4) ?
C34 C54 C53 ? ? ? 88.35 ?
O35 C54 C53 ? ? ? 133.2(4) ?


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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?

#=============================================================================

#=============================================================================
# Additional structures (last six sections and associated data_? identifiers) 
# may be added at this point.                                                 
#=============================================================================

# The following lines are used to test the character set of files sent by     
# network email or other means. They are not part of the CIF data set.        
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789              
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ 
####################################################################### 
# 
# 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_squaramide_1c
_database_code_depnum_ccdc_archive 'CCDC 1584438'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_name_systematic        
;
bis([1,2,3]triazolo)[1,5-a:5',1'-k][1,10]phenanthroline 
;
_chemical_formula_moiety         'C12 H22 N4 O2'
_chemical_formula_sum            'C12 H22 N4 O2'
_chemical_formula_weight         254.34


#==============================================================================
# POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_symmetry_int_tables_number      15

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   29.6240(17)
_cell_length_b                   6.0611(2)
_cell_length_c                   8.6488(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.974(4)
_cell_angle_gamma                90.0000
_cell_volume                     1519.14(12)


_cell_formula_units_Z            4
_cell_measurement_temperature    333 #REVISAR: ES CERT?
_exptl_crystal_density_diffrn    1.112

_pd_spec_mounting                'glass capillary'
_pd_spec_mount_mode              transmission
_pd_char_colour                  ? #REVISAR: color de la pols

_exptl_crystal_F_000             552.0
_exptl_absorpt_coefficient_mu    0.630

#==============================================================================
# EXPERIMENTAL DATA



_diffrn_ambient_temperature      333 #REVISAR: ES CERT?
_diffrn_radiation_type           'Cu K\a'
_pd_meas_scan_method             
continuous # REVISAR: \~A?s aix\~A? oi per aquest detector?
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 X'Celerator

loop_
_diffrn_radiation_wavelength.id
_diffrn_radiation_wavelength.wavelength
_diffrn_radiation_wavelength.wt
K\a1 1.54059 1.0
K\a2 1.54439 0.5

_pd_meas_number_of_points        5227
_pd_meas_2theta_range_min        2.03100
_pd_meas_2theta_range_max        69.98206
_pd_meas_2theta_range_inc        0.01300

_computing_data_reduction        'DAJUST (Vallcorba et al., 2012)'
_computing_structure_solution    'TALP (Vallcorba et al., 2012)'
_computing_structure_refinement  'RIBOLS (Rius, 2012)'
_computing_publication_material  'PLATON (Spek, 2003)'

#==============================================================================
# REFINEMENT DATA

_pd_proc_ls_profile_function     Pseudo-Voigt
_pd_proc_ls_background_function  
'Smoothing procedure. Br\~A1/4ckner, S. (2000). J. Appl. Cryst., 33, 977-979'

_pd_proc_ls_prof_wR_factor       0.102
_refine_ls_R_I_factor            0.039
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     1/Yobs
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         662
_refine_ls_number_parameters     38
_refine_ls_number_restraints     28
_refine_ls_goodness_of_fit_all   10.589
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.049
_refine_diff_density_max         0.012
_refine_diff_density_min         -0.016

_pd_proc_number_of_points        5075
_pd_proc_2theta_range_min        4.01300
_pd_proc_2theta_range_max        69.98206
_pd_proc_2theta_range_inc        0.01300


#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
O1 O 0.0437(2) -0.1337(12) 0.1562(4) 1.0000 0.073(2)
N1 N 0.0418(2) 0.4048(9) 0.1577(4) 1.0000 0.073(2)
N2 N 0.1605(2) 0.3255(10) 0.0875(4) 1.0000 0.073(2)
C1 C 0.0197(1) 0.0033(12) 0.2085(4) 1.0000 0.073(2)
C2 C 0.0186(1) 0.2471(12) 0.2101(4) 1.0000 0.073(2)
C3 C 0.0781(2) 0.3572(16) 0.0739(4) 1.0000 0.073(2)
C4 C 0.1255(2) 0.3701(17) 0.1794(4) 1.0000 0.073(2)
C5 C 0.1664(3) 0.0864(9) 0.0760(4) 1.0000 0.073(2)
C6 C 0.2050(2) 0.4204(13) 0.1635(4) 1.0000 0.073(2)
H1 H 0.0350 0.5400 0.1729 1.0000 0.073
H2a H 0.0758 0.4567 -0.0153 1.0000 0.073
H2b H 0.0739 0.2079 0.0330 1.0000 0.073
H3a H 0.1298 0.5184 0.2220 1.0000 0.073
H3b H 0.1284 0.2676 0.2671 1.0000 0.073
H5a H 0.1373 0.0219 0.0274 1.0000 0.073
H5b H 0.1767 0.0247 0.1796 1.0000 0.073
H5c H 0.1888 0.0556 0.0128 1.0000 0.073
H6a H 0.2149 0.3598 0.2676 1.0000 0.073
H6b H 0.2274 0.3861 0.1011 1.0000 0.073
H6c H 0.2021 0.5776 0.1706 1.0000 0.073


#===============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.238(8) . . yes
N1 C2 1.312(8) . . yes
N1 C3 1.445(8) . . yes
N2 C4 1.457(8) . . yes
N2 C5 1.466(8) . . yes
N2 C6 1.463(8) . . yes
C1 C2 1.478(10) . . no
C1 C1 1.492(4) . 2_555 no
N1 H1 0.8600 . . no
C2 C2 1.417(4) . 2_555 no
C3 C4 1.510(7) . . no
C3 H2A 0.9700 . . no
C3 H2B 0.9700 . . no
C4 H3A 0.9700 . . no
C4 H3B 0.9700 . . no
C5 H5A 0.9600 . . no
C5 H5B 0.9600 . . no
C5 H5C 0.9600 . . no
C6 H6A 0.9600 . . no
C6 H6B 0.9600 . . no
C6 H6C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 121.7(6) . . . yes
C4 N2 C5 109.2(6) . . . yes
C4 N2 C6 111.0(4) . . . yes
C5 N2 C6 108.1(6) . . . yes
O1 C1 C2 133.6(5) . . . yes
O1 C1 C1 137.9(7) . . 2_555 yes
C1 C1 C2 88.5(4) 2_555 . . no
C3 N1 H1 119.00 . . . no
C2 N1 H1 119.00 . . . no
N1 C2 C2 133.2(6) . . 2_555 yes
N1 C2 C1 135.3(4) . . . yes
C1 C2 C2 91.5(5) . . 2_555 no
N1 C3 C4 112.5(4) . . . yes
N2 C4 C3 109.8(4) . . . yes
N1 C3 H2A 110.00 . . . no
N1 C3 H2B 108.00 . . . no
C4 C3 H2A 111.00 . . . no
C4 C3 H2B 108.00 . . . no
H2A C3 H2B 108.00 . . . no
N2 C4 H3A 109.00 . . . no
N2 C4 H3B 110.00 . . . no
C3 C4 H3A 108.00 . . . no
C3 C4 H3B 111.00 . . . no
H3A C4 H3B 108.00 . . . no
N2 C5 H5A 109.00 . . . no
N2 C5 H5B 110.00 . . . no
N2 C5 H5C 110.00 . . . no
H5A C5 H5B 109.00 . . . no
H5A C5 H5C 110.00 . . . no
H5B C5 H5C 109.00 . . . no
N2 C6 H6A 110.00 . . . no
N2 C6 H6B 109.00 . . . no
N2 C6 H6C 110.00 . . . no
H6A C6 H6B 109.00 . . . no
H6A C6 H6C 109.00 . . . no
H6B C6 H6C 109.00 . . . no

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
C3 N1 C2 C1 0.9(7) . . . . no
C3 N1 C2 C2 -177.9(4) . . . 2_555 no
C2 N1 C3 C4 -98.5(8) . . . . no
C5 N2 C4 C3 -83.9(8) . . . . no
C6 N2 C4 C3 157.0(7) . . . . no
O1 C1 C2 N1 0.4(7) . . . . no
O1 C1 C2 C2 179.5(4) . . . 2_555 no
C1 C1 C2 N1 -178.7(4) 2_555 . . . no
C1 C1 C2 C2 0.4(3) 2_555 . . 2_555 no
O1 C1 C1 O1 1.6(8) . . 2_555 2_555 no
O1 C1 C1 C2 -179.4(5) . . 2_555 2_555 no
C2 C1 C1 O1 -179.4(5) . . 2_555 2_555 no
C2 C1 C1 C2 -0.4(3) . . 2_555 2_555 no
N1 C2 C2 N1 -2.1(7) . . 2_555 2_555 no
N1 C2 C2 C1 178.8(4) . . 2_555 2_555 no
C1 C2 C2 N1 178.8(4) . . 2_555 2_555 no
C1 C2 C2 C1 -0.4(3) . . 2_555 2_555 no
N1 C3 C4 N2 -178.7(7) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O1 0.8600 2.0000 2.798(9) 153.00 1_565 yes
####################################################################### 
# 
# 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_anom71a
_audit_block_doi                 10.5517/cc132vz0
_database_code_depnum_ccdc_archive 'CCDC 1015652'
_audit_update_record             
;
2014-07-23 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 O2'
_chemical_formula_sum            'C12 H22 N4 O2'
_chemical_formula_weight         254.34

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   16.185(14)
_cell_length_b                   29.012(18)
_cell_length_c                   6.093(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2861(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    613
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with an image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5245
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         32.42
_reflns_number_total             1961
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MARXDS
_computing_cell_refinement       AUTOMAR
_computing_data_reduction        MARSCALE
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0998P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         1961
_refine_ls_number_parameters     85
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2027
_refine_ls_wR_factor_gt          0.1901
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.139
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40176(13) 0.01176(6) -0.2334(3) 0.0579(5) Uani 1 1 d . . .
N1 N 0.32776(16) 0.10788(9) 0.2766(5) 0.0687(6) Uani 1 1 d U . .
N2 N 0.40192(14) 0.01259(7) 0.3036(3) 0.0494(5) Uani 1 1 d D . .
H2N H 0.4168(19) 0.0127(11) 0.447(2) 0.059 Uiso 1 1 d D . .
C1 C 0.3141(3) 0.11619(18) 0.0443(8) 0.1023(13) Uani 1 1 d U . .
H1A H 0.3330 0.0901 -0.0386 0.154 Uiso 1 1 calc R . .
H1B H 0.3440 0.1432 -0.0002 0.154 Uiso 1 1 calc R . .
H1C H 0.2562 0.1208 0.0182 0.154 Uiso 1 1 calc R . .
C2 C 0.2992(3) 0.14756(17) 0.4025(9) 0.1086(15) Uani 1 1 d . . .
H2A H 0.3085 0.1421 0.5560 0.163 Uiso 1 1 calc R . .
H2B H 0.2412 0.1521 0.3770 0.163 Uiso 1 1 calc R . .
H2C H 0.3291 0.1745 0.3574 0.163 Uiso 1 1 calc R . .
C3 C 0.2843(2) 0.06619(11) 0.3541(6) 0.0697(8) Uani 1 1 d U . .
H3A H 0.2257 0.0695 0.3241 0.084 Uiso 1 1 calc R . .
H3B H 0.2911 0.0637 0.5118 0.084 Uiso 1 1 calc R . .
C4 C 0.31520(16) 0.02230(9) 0.2474(4) 0.0529(6) Uani 1 1 d U . .
H4A H 0.2810 -0.0033 0.2945 0.064 Uiso 1 1 calc R . .
H4B H 0.3100 0.0250 0.0894 0.064 Uiso 1 1 calc R . .
C5 C 0.45752(15) 0.00566(9) 0.1485(4) 0.0448(6) Uani 1 1 d . . .
C6 C 0.45465(17) 0.00515(9) -0.0943(4) 0.0476(6) 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
O1 C6 1.220(3) . ?
N1 C1 1.453(6) . ?
N1 C2 1.459(5) . ?
N1 C3 1.477(4) . ?
N2 C5 1.320(3) . ?
N2 C4 1.472(4) . ?
N2 H2N 0.905(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.414(5) 2_655 ?
C5 C6 1.480(3) . ?
C6 C6 1.498(6) 2_655 ?

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
C1 N1 C2 109.5(3) . . ?
C1 N1 C3 112.0(3) . . ?
C2 N1 C3 109.1(3) . . ?
C5 N2 C4 120.8(2) . . ?
C5 N2 H2N 121(2) . . ?
C4 N2 H2N 118(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 113.2(3) . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C3 112.1(2) . . ?
N2 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N2 C5 C5 134.29(15) . 2_655 ?
N2 C5 C6 134.1(3) . . ?
C5 C5 C6 91.62(16) 2_655 . ?
O1 C6 C5 135.6(3) . . ?
O1 C6 C6 135.99(16) . 2_655 ?
C5 C6 C6 88.35(16) . 2_655 ?

_diffrn_measured_fraction_theta_max 0.850
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_mo_023tb167_0m
_database_code_depnum_ccdc_archive 'CCDC 1584388'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        N,N?-bis(2-(dimethylamino)ethyl)squaramide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 O2'
_chemical_formula_sum            'C12 H22 N4 O2'
_chemical_formula_weight         254.33

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                   6.0552(3)
_cell_length_b                   14.4565(8)
_cell_length_c                   15.8765(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.773(2)
_cell_angle_gamma                90
_cell_volume                     1377.01(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9613
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43180
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.590
_diffrn_reflns_theta_max         29.645
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3866
_reflns_number_gt                3330
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0585P)²+0.6591P] 
 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         3866
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 1.26304(12) 0.37742(6) 0.51414(5) 0.01685(17) Uani 1 1 d . . . . .
O2 O 1.19026(12) 0.45754(6) 0.32040(5) 0.01802(18) Uani 1 1 d . . . . .
N1 N 0.67884(15) 0.64591(7) 0.16413(6) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.65038(15) 0.45421(6) 0.32082(6) 0.01471(19) Uani 1 1 d . . . . .
H5N H 0.5164 0.4432 0.3341 0.018 Uiso 1 1 calc R U . . .
N3 N 0.72329(14) 0.37569(6) 0.51510(6) 0.01335(18) Uani 1 1 d . . . . .
H4N H 0.5811 0.3898 0.5032 0.016 Uiso 1 1 calc R U . . .
N4 N 0.87091(15) 0.17655(7) 0.53440(6) 0.0174(2) Uani 1 1 d . . . . .
C1 C 0.9182(2) 0.66381(9) 0.17306(8) 0.0251(3) Uani 1 1 d . . . . .
H1A H 0.9564 0.6907 0.1202 0.038 Uiso 1 1 calc R U . . .
H1B H 0.9996 0.6056 0.1849 0.038 Uiso 1 1 calc R U . . .
H1C H 0.9592 0.7071 0.2200 0.038 Uiso 1 1 calc R U . . .
C2 C 0.61715(18) 0.59924(8) 0.23902(7) 0.0160(2) Uani 1 1 d . . . . .
H2A H 0.4553 0.6070 0.2405 0.019 Uiso 1 1 calc R U . . .
H2B H 0.6974 0.6282 0.2908 0.019 Uiso 1 1 calc R U . . .
C3 C 0.67288(18) 0.49636(7) 0.23872(7) 0.0154(2) Uani 1 1 d . . . . .
H3A H 0.5715 0.4650 0.1934 0.018 Uiso 1 1 calc R U . . .
H3B H 0.8275 0.4881 0.2262 0.018 Uiso 1 1 calc R U . . .
C4 C 0.82692(16) 0.43229(7) 0.37544(7) 0.0125(2) Uani 1 1 d . . . . .
C5 C 0.85843(16) 0.39664(7) 0.45967(7) 0.0121(2) Uani 1 1 d . . . . .
C6 C 0.80049(17) 0.32986(7) 0.59570(7) 0.0148(2) Uani 1 1 d . . . . .
H6A H 0.7291 0.3591 0.6416 0.018 Uiso 1 1 calc R U . . .
H6B H 0.9637 0.3380 0.6095 0.018 Uiso 1 1 calc R U . . .
C7 C 0.74556(18) 0.22698(8) 0.59185(7) 0.0168(2) Uani 1 1 d . . . . .
H7A H 0.7788 0.2003 0.6496 0.020 Uiso 1 1 calc R U . . .
H7B H 0.5841 0.2190 0.5728 0.020 Uiso 1 1 calc R U . . .
C8 C 0.7622(2) 0.08931(8) 0.50734(8) 0.0229(2) Uani 1 1 d . . . . .
H8A H 0.7603 0.0489 0.5568 0.034 Uiso 1 1 calc R U . . .
H8B H 0.8444 0.0591 0.4659 0.034 Uiso 1 1 calc R U . . .
H8C H 0.6089 0.1015 0.4812 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0998(2) 0.15964(9) 0.57351(9) 0.0254(3) Uani 1 1 d . . . . .
H9A H 1.1725 0.2187 0.5899 0.038 Uiso 1 1 calc R U . . .
H9B H 1.1816 0.1280 0.5328 0.038 Uiso 1 1 calc R U . . .
H9C H 1.0987 0.1209 0.6241 0.038 Uiso 1 1 calc R U . . .
C10 C 1.10110(16) 0.39724(7) 0.46125(7) 0.0133(2) Uani 1 1 d . . . . .
C11 C 1.06792(16) 0.43411(7) 0.37287(7) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.5591(2) 0.73326(9) 0.15076(9) 0.0273(3) Uani 1 1 d . . . . .
H12A H 0.5963 0.7729 0.2007 0.041 Uiso 1 1 calc R U . . .
H12B H 0.3983 0.7213 0.1420 0.041 Uiso 1 1 calc R U . . .
H12C H 0.6021 0.7643 0.1006 0.041 Uiso 1 1 calc R U . . .


_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
O1 C10 1.2354(13) . ?
O2 C11 1.2346(13) . ?
N1 C12 1.4574(15) . ?
N1 C2 1.4589(14) . ?
N1 C1 1.4602(15) . ?
N2 C4 1.3207(13) . ?
N2 C3 1.4619(13) . ?
N2 H5N 0.8800 . ?
N3 C5 1.3155(13) . ?
N3 C6 1.4606(13) . ?
N3 H4N 0.8800 . ?
N4 C7 1.4584(14) . ?
N4 C8 1.4600(15) . ?
N4 C9 1.4604(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5253(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.4216(14) . ?
C4 C11 1.4656(14) . ?
C5 C10 1.4663(14) . ?
C6 C7 1.5233(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4889(15) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C12 N1 C2 110.01(9) . . ?
C12 N1 C1 109.18(10) . . ?
C2 N1 C1 111.28(9) . . ?
C4 N2 C3 121.38(9) . . ?
C4 N2 H5N 119.3 . . ?
C3 N2 H5N 119.3 . . ?
C5 N3 C6 122.43(9) . . ?
C5 N3 H4N 118.8 . . ?
C6 N3 H4N 118.8 . . ?
C7 N4 C8 111.33(9) . . ?
C7 N4 C9 111.22(9) . . ?
C8 N4 C9 110.16(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 111.54(9) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C2 110.87(9) . . ?
N2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C5 134.29(9) . . ?
N2 C4 C11 134.26(10) . . ?
C5 C4 C11 91.45(8) . . ?
N3 C5 C4 134.12(9) . . ?
N3 C5 C10 134.63(10) . . ?
C4 C5 C10 91.18(8) . . ?
N3 C6 C7 111.43(9) . . ?
N3 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 C6 112.58(9) . . ?
N4 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N4 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C5 135.38(10) . . ?
O1 C10 C11 135.82(10) . . ?
C5 C10 C11 88.79(8) . . ?
O2 C11 C4 135.59(10) . . ?
O2 C11 C10 135.82(9) . . ?
C4 C11 C10 88.58(8) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C12 N1 C2 C3 160.67(9) . . . . ?
C1 N1 C2 C3 -78.19(12) . . . . ?
C4 N2 C3 C2 -104.98(11) . . . . ?
N1 C2 C3 N2 169.17(8) . . . . ?
C3 N2 C4 C5 175.67(11) . . . . ?
C3 N2 C4 C11 -5.14(18) . . . . ?
C6 N3 C5 C4 173.12(11) . . . . ?
C6 N3 C5 C10 -10.69(18) . . . . ?
N2 C4 C5 N3 -3.0(2) . . . . ?
C11 C4 C5 N3 177.56(12) . . . . ?
N2 C4 C5 C10 179.69(12) . . . . ?
C11 C4 C5 C10 0.28(8) . . . . ?
C5 N3 C6 C7 -101.31(11) . . . . ?
C8 N4 C7 C6 -158.95(9) . . . . ?
C9 N4 C7 C6 77.79(12) . . . . ?
N3 C6 C7 N4 67.46(11) . . . . ?
N3 C5 C10 O1 1.1(2) . . . . ?
C4 C5 C10 O1 178.37(13) . . . . ?
N3 C5 C10 C11 -177.53(12) . . . . ?
C4 C5 C10 C11 -0.27(8) . . . . ?
N2 C4 C11 O2 1.3(2) . . . . ?
C5 C4 C11 O2 -179.30(13) . . . . ?
N2 C4 C11 C10 -179.69(12) . . . . ?
C5 C4 C11 C10 -0.27(8) . . . . ?
O1 C10 C11 O2 0.7(2) . . . . ?
C5 C10 C11 O2 179.29(13) . . . . ?
O1 C10 C11 C4 -178.37(13) . . . . ?
C5 C10 C11 C4 0.26(8) . . . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.074

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
