# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1886021'
loop_
_audit_author_name
_audit_author_address
'Cobo Justo'
;Universidad de Jaen
Spain
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_date             2019-08-13T08:39:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
2-(4-(4-Methoxyphenyl)-3-methyl-1-phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-ylidene)malononitrile'
_chemical_formula_sum            'C30 H19 N5 O'
_chemical_formula_weight         465.5
_chemical_melting_point          518.0(10)
_chemical_compound_source        'synthetized by authors'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.878(7)
_cell_length_b                   12.149(6)
_cell_length_c                   27.262(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.052(12)
_cell_angle_gamma                90
_cell_volume                     4900(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.345
_cell_measurement_theta_max      27.32
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             1936
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
;
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_T_max  0.7456
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.986

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source_type              
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_detector_type            'CMOS Photon 100'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_number            70587
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        27.496
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5639
_reflns_number_gt                4245
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 v2016.1--0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'mercury 3.10.3'
_computing_publication_material  'wingx v2018.2'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;disorder solvent was found at four sites in unit cell,
but it could not be properly modelled. Several peaks of
about 6 to 8 e were found but without any posibility of
modelling in different positions at asymmetric unit, so 
SQUEZEE in platon was run to generate a new hkl file.
The volumen void and the total recovered electron suggest
more than one molecule of solvent so DMF (40 e) and/or
water (10 e) occupying such volumen.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+12.4144P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5639
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.09
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.07


# SQUEEZE RESULTS (Version = 260918)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 0.104 0.250 153 57 ' '
2 1.000 -0.105 0.750 153 57 ' '
3 0.500 0.395 0.750 153 57 ' '
4 0.500 0.604 0.250 153 57 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?



#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O44 O 0.12782(12) 0.38018(16) 0.25106(6) 0.0306(4) Uani 1 1 d . . . . .
N10 N 0.11566(12) 0.51624(15) 0.55654(6) 0.0137(4) Uani 1 1 d . . . . .
N1 N 0.11740(12) 0.31836(15) 0.56144(6) 0.0140(4) Uani 1 1 d . . . . .
N2 N 0.12100(12) 0.23030(15) 0.52943(6) 0.0157(4) Uani 1 1 d . . . . .
N53 N 0.17648(15) 0.93216(18) 0.38116(8) 0.0287(5) Uani 1 1 d . . . . .
N52 N 0.20747(17) 0.63785(18) 0.32785(8) 0.0330(6) Uani 1 1 d . . . . .
C008 C 0.13251(13) 0.38962(18) 0.48749(8) 0.0130(4) Uani 1 1 d . . . . .
C009 C 0.12301(13) 0.41496(18) 0.53699(7) 0.0132(4) Uani 1 1 d . . . . .
C00A C 0.13344(13) 0.58187(18) 0.47244(7) 0.0127(4) Uani 1 1 d . . . . .
C00B C 0.12098(13) 0.59487(18) 0.52365(7) 0.0130(4) Uani 1 1 d . . . . .
C4 C 0.13683(13) 0.47631(18) 0.45320(7) 0.0126(4) Uani 1 1 d . . . . .
C00D C 0.11472(14) 0.71170(18) 0.53513(8) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.10760(14) 0.29984(19) 0.61227(8) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.12989(14) 0.27203(18) 0.48536(8) 0.0146(4) Uani 1 1 d . . . . .
C46 C 0.05983(15) 0.46796(18) 0.36792(8) 0.0161(5) Uani 1 1 d . . . . .
H46 H 0.008659 0.497539 0.379776 0.019 Uiso 1 1 calc R U . . .
C41 C 0.13797(14) 0.45007(18) 0.40009(7) 0.0128(4) Uani 1 1 d . . . . .
C51 C 0.16293(14) 0.72799(19) 0.40682(8) 0.0158(5) Uani 1 1 d . . . . .
C00K C 0.12466(14) 0.77234(18) 0.49213(8) 0.0149(4) Uani 1 1 d . . . . .
C5 C 0.14034(14) 0.69411(18) 0.45173(8) 0.0138(4) Uani 1 1 d . . . . .
C45 C 0.05848(15) 0.44183(19) 0.31863(8) 0.0191(5) Uani 1 1 d . . . . .
H45 H 0.006212 0.452999 0.297337 0.023 Uiso 1 1 calc R U . . .
C12 C 0.05768(14) 0.2104(2) 0.62551(8) 0.0186(5) Uani 1 1 d . . . . .
H12 H 0.031123 0.162573 0.601595 0.022 Uiso 1 1 calc R U . . .
C16 C 0.14862(15) 0.37135(19) 0.64751(8) 0.0181(5) Uani 1 1 d . . . . .
H16 H 0.18322 0.430111 0.638304 0.022 Uiso 1 1 calc R U . . .
C53 C 0.16995(15) 0.8432(2) 0.39436(8) 0.0189(5) Uani 1 1 d . . . . .
C43 C 0.21238(15) 0.3782(2) 0.33235(8) 0.0192(5) Uani 1 1 d . . . . .
H43 H 0.263245 0.348197 0.320353 0.023 Uiso 1 1 calc R U . . .
C42 C 0.21304(14) 0.40287(19) 0.38217(8) 0.0172(5) Uani 1 1 d . . . . .
H42 H 0.26422 0.387632 0.403712 0.021 Uiso 1 1 calc R U . . .
C9 C 0.10151(15) 0.76161(19) 0.57944(8) 0.0178(5) Uani 1 1 d . . . . .
H9 H 0.095447 0.720025 0.607545 0.021 Uiso 1 1 calc R U . . .
C31 C 0.13713(16) 0.19577(19) 0.44281(8) 0.0186(5) Uani 1 1 d . . . . .
H31A H 0.198178 0.195679 0.434382 0.028 Uiso 1 1 calc R U . . .
H31B H 0.097199 0.220079 0.414958 0.028 Uiso 1 1 calc R U . . .
H31C H 0.120672 0.12267 0.451808 0.028 Uiso 1 1 calc R U . . .
C52 C 0.18560(16) 0.66552(19) 0.36498(8) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.09758(16) 0.8762(2) 0.58060(9) 0.0208(5) Uani 1 1 d . . . . .
H8 H 0.089545 0.9119 0.610007 0.025 Uiso 1 1 calc R U . . .
C44 C 0.13507(16) 0.39891(19) 0.30079(8) 0.0190(5) Uani 1 1 d . . . . .
C15 C 0.13701(16) 0.3535(2) 0.69691(8) 0.0217(5) Uani 1 1 d . . . . .
H15 H 0.163094 0.401441 0.720916 0.026 Uiso 1 1 calc R U . . .
C7 C 0.10551(16) 0.93749(19) 0.53851(8) 0.0218(5) Uani 1 1 d . . . . .
H7 H 0.101226 1.013785 0.539823 0.026 Uiso 1 1 calc R U . . .
C6 C 0.11987(16) 0.88654(19) 0.49401(9) 0.0204(5) Uani 1 1 d . . . . .
H6 H 0.12613 0.928487 0.466033 0.024 Uiso 1 1 calc R U . . .
C14 C 0.08673(15) 0.2645(2) 0.71044(8) 0.0246(6) Uani 1 1 d . . . . .
H14 H 0.079276 0.25303 0.743495 0.03 Uiso 1 1 calc R U . . .
C13 C 0.04783(16) 0.1933(2) 0.67518(9) 0.0245(5) Uani 1 1 d . . . . .
H13 H 0.014775 0.133268 0.684554 0.029 Uiso 1 1 calc R U . . .
C47 C 0.2091(2) 0.3523(3) 0.22958(10) 0.0577(11) Uani 1 1 d . . . . .
H47A H 0.25568 0.404306 0.240245 0.087 Uiso 1 1 calc R U . . .
H47B H 0.197563 0.354365 0.194279 0.087 Uiso 1 1 calc R U . . .
H47C H 0.228224 0.279704 0.239893 0.087 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O44 C44 1.368(3) . ?
O44 C47 1.438(3) . ?
N10 C00B 1.318(3) . ?
N10 C009 1.350(3) . ?
N1 C009 1.357(3) . ?
N1 N2 1.385(3) . ?
N1 C11 1.426(3) . ?
N2 C3 1.324(3) . ?
N53 C53 1.146(3) . ?
N52 C52 1.146(3) . ?
C008 C009 1.406(3) . ?
C008 C4 1.414(3) . ?
C008 C3 1.430(3) . ?
C00A C4 1.388(3) . ?
C00A C00B 1.436(3) . ?
C00A C5 1.484(3) . ?
C00B C00D 1.459(3) . ?
C4 C41 1.484(3) . ?
C00D C9 1.384(3) . ?
C00D C00K 1.406(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.388(3) . ?
C3 C31 1.497(3) . ?
C46 C45 1.379(3) . ?
C46 C41 1.398(3) . ?
C46 H46 0.93 . ?
C41 C42 1.389(3) . ?
C51 C5 1.367(3) . ?
C51 C52 1.439(3) . ?
C51 C53 1.447(3) . ?
C00K C6 1.390(3) . ?
C00K C5 1.492(3) . ?
C45 C44 1.387(3) . ?
C45 H45 0.93 . ?
C12 C13 1.393(3) . ?
C12 H12 0.93 . ?
C16 C15 1.393(3) . ?
C16 H16 0.93 . ?
C43 C44 1.385(3) . ?
C43 C42 1.390(3) . ?
C43 H43 0.93 . ?
C42 H42 0.93 . ?
C9 C8 1.394(3) . ?
C9 H9 0.93 . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C8 C7 1.383(3) . ?
C8 H8 0.93 . ?
C15 C14 1.386(4) . ?
C15 H15 0.93 . ?
C7 C6 1.398(3) . ?
C7 H7 0.93 . ?
C6 H6 0.93 . ?
C14 C13 1.375(4) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?
C47 H47A 0.96 . ?
C47 H47B 0.96 . ?
C47 H47C 0.96 . ?

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
C44 O44 C47 117.44(19) . . ?
C00B N10 C009 112.25(18) . . ?
C009 N1 N2 110.49(17) . . ?
C009 N1 C11 129.18(18) . . ?
N2 N1 C11 120.33(17) . . ?
C3 N2 N1 106.88(18) . . ?
C009 C008 C4 119.19(19) . . ?
C009 C008 C3 104.64(18) . . ?
C4 C008 C3 136.0(2) . . ?
N10 C009 N1 125.64(19) . . ?
N10 C009 C008 126.81(19) . . ?
N1 C009 C008 107.46(19) . . ?
C4 C00A C00B 118.83(19) . . ?
C4 C00A C5 134.31(19) . . ?
C00B C00A C5 106.86(18) . . ?
N10 C00B C00A 127.2(2) . . ?
N10 C00B C00D 123.32(19) . . ?
C00A C00B C00D 109.48(18) . . ?
C00A C4 C008 115.60(19) . . ?
C00A C4 C41 124.85(19) . . ?
C008 C4 C41 119.40(19) . . ?
C9 C00D C00K 122.4(2) . . ?
C9 C00D C00B 129.2(2) . . ?
C00K C00D C00B 108.44(19) . . ?
C12 C11 C16 121.3(2) . . ?
C12 C11 N1 119.3(2) . . ?
C16 C11 N1 119.4(2) . . ?
N2 C3 C008 110.52(19) . . ?
N2 C3 C31 119.2(2) . . ?
C008 C3 C31 130.2(2) . . ?
C45 C46 C41 120.1(2) . . ?
C45 C46 H46 120 . . ?
C41 C46 H46 120 . . ?
C42 C41 C46 119.34(19) . . ?
C42 C41 C4 121.60(19) . . ?
C46 C41 C4 118.97(18) . . ?
C5 C51 C52 130.6(2) . . ?
C5 C51 C53 122.2(2) . . ?
C52 C51 C53 107.18(19) . . ?
C6 C00K C00D 118.8(2) . . ?
C6 C00K C5 132.5(2) . . ?
C00D C00K C5 108.68(19) . . ?
C51 C5 C00A 130.6(2) . . ?
C51 C5 C00K 122.8(2) . . ?
C00A C5 C00K 106.39(17) . . ?
C46 C45 C44 120.0(2) . . ?
C46 C45 H45 120 . . ?
C44 C45 H45 120 . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C11 C16 C15 118.8(2) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
N53 C53 C51 175.1(2) . . ?
C44 C43 C42 119.2(2) . . ?
C44 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
C41 C42 C43 120.6(2) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C00D C9 C8 117.9(2) . . ?
C00D C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N52 C52 C51 165.2(2) . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
O44 C44 C43 124.0(2) . . ?
O44 C44 C45 115.36(19) . . ?
C43 C44 C45 120.6(2) . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C00K C6 C7 119.1(2) . . ?
C00K C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O44 C47 H47A 109.5 . . ?
O44 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O44 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?

# 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
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_formula_moiety         'C30 H19 N5 O'
