#------------------------------------------------------------------------------
#$Date: 2021-01-07 08:29:10 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260781 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/44/7704412.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7704412
loop_
_publ_author_name
'Rowland, Casey A.'
'Yap, Glenn P. A.'
'Bloch, Eric D.'
_publ_section_title
;
 Novel syntheses of carbazole-3,6-dicarboxylate ligands and their
 utilization for porous coordination cages.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16340
_journal_page_last               16347
_journal_paper_doi               10.1039/d0dt01149e
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C23 H19 N O4'
_chemical_formula_sum            'C23 H19 N O4'
_chemical_formula_weight         373.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-03-22
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-11 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.784(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5221(7)
_cell_length_b                   18.6073(14)
_cell_length_c                   11.5804(8)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.38
_cell_measurement_theta_min      2.81
_cell_volume                     1836.2(2)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Diamond (Putz & Brandenburg, 1997)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            86509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.451
_diffrn_reflns_theta_min         2.072
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1414 before and 0.0406 after correction.
The Ratio of minimum to maximum transmission is 0.9462.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method
'Slow evaporation from saturated solution in DMF.'
_exptl_crystal_size_max          0.693
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.312
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         8960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1013P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7542
_reflns_number_total             8985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01149e2.cif
_cod_data_source_block           eric412
_cod_depositor_comments
'Adding full bibliography for 7704412--7704415.cif.'
_cod_database_code               7704412
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_olex2_exptl_crystal_mounting_method 'Mounted with mother liquor at 100K.'
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.10326(7) 0.47039(3) 0.34848(5) 0.02479(11) Uani 1 1 d . . . . .
O2 O 0.19888(7) 0.57342(3) 0.42222(5) 0.02650(11) Uani 1 1 d . . . . .
O3 O 0.70778(8) 0.66361(3) 0.92824(5) 0.02889(12) Uani 1 1 d . . . . .
O4 O 0.83910(7) 0.59809(3) 1.06090(5) 0.02746(12) Uani 1 1 d . . . . .
N1 N 0.48498(7) 0.35231(3) 0.78152(5) 0.01956(10) Uani 1 1 d . . . . .
C1 C 0.02225(9) 0.51270(5) 0.26195(7) 0.02771(14) Uani 1 1 d . . . . .
H1A H -0.033397 0.480699 0.208091 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.098421 0.541630 0.219607 0.042 Uiso 1 1 calc GR . . . .
H1C H -0.053306 0.544505 0.299388 0.042 Uiso 1 1 calc GR . . . .
C2 C 0.18920(7) 0.50828(4) 0.42492(6) 0.01934(11) Uani 1 1 d . . . . .
C3 C 0.42756(7) 0.45597(3) 0.68428(5) 0.01725(10) Uani 1 1 d . . . . .
C4 C 0.35751(7) 0.49690(3) 0.59746(5) 0.01790(10) Uani 1 1 d . . . . .
C5 C 0.26759(7) 0.46230(3) 0.51279(5) 0.01805(11) Uani 1 1 d . . . . .
C6 C 0.25021(8) 0.38678(4) 0.51390(6) 0.02091(11) Uani 1 1 d . . . . .
C7 C 0.31942(8) 0.34473(3) 0.59989(6) 0.02109(12) Uani 1 1 d . . . . .
C8 C 0.40677(7) 0.38033(3) 0.68591(6) 0.01837(11) Uani 1 1 d . . . . .
C9 C 0.52621(7) 0.47359(3) 0.78273(5) 0.01743(10) Uani 1 1 d . . . . .
C10 C 0.58612(8) 0.53781(3) 0.82627(6) 0.01867(11) Uani 1 1 d . . . . .
C11 C 0.68033(8) 0.53584(3) 0.92591(6) 0.01911(11) Uani 1 1 d . . . . .
C12 C 0.71364(8) 0.47003(4) 0.98151(6) 0.02054(11) Uani 1 1 d . . . . .
C13 C 0.65457(8) 0.40524(3) 0.93954(6) 0.02040(11) Uani 1 1 d . . . . .
C14 C 0.55999(8) 0.40788(3) 0.83985(6) 0.01825(11) Uani 1 1 d . . . . .
C15 C 0.74144(8) 0.60553(4) 0.96986(6) 0.02055(11) Uani 1 1 d . . . . .
C16 C 0.90481(10) 0.66395(4) 1.10711(7) 0.02807(14) Uani 1 1 d . . . . .
H16A H 0.983290 0.682719 1.053899 0.042 Uiso 1 1 calc GR . . . .
H16B H 0.954591 0.654250 1.182291 0.042 Uiso 1 1 calc GR . . . .
H16C H 0.821043 0.699474 1.116448 0.042 Uiso 1 1 calc GR . . . .
C17 C 0.49925(8) 0.27684(3) 0.81188(6) 0.02096(12) Uani 1 1 d . . . . .
C18 C 0.72262(8) 0.19349(3) 0.86009(6) 0.02113(12) Uani 1 1 d . . . . .
C19 C 0.86900(9) 0.16358(4) 0.83822(7) 0.02590(13) Uani 1 1 d . . . . .
C20 C 0.95489(9) 0.18701(4) 0.74396(8) 0.02871(14) Uani 1 1 d . . . . .
C21 C 0.89397(10) 0.24068(5) 0.67244(7) 0.02888(15) Uani 1 1 d . . . . .
C22 C 0.74671(9) 0.27033(4) 0.69391(6) 0.02432(13) Uani 1 1 d . . . . .
C23 C 0.65998(8) 0.24638(3) 0.78769(5) 0.01834(11) Uani 1 1 d . . . . .
H4 H 0.3725(16) 0.5477(8) 0.5959(12) 0.030(3) Uiso 1 1 d . . . . .
H6 H 0.1813(15) 0.3640(8) 0.4514(11) 0.030(3) Uiso 1 1 d . . . . .
H7 H 0.3073(17) 0.2943(8) 0.5981(13) 0.038(3) Uiso 1 1 d . . . . .
H10 H 0.5639(15) 0.5880(7) 0.7861(11) 0.028(3) Uiso 1 1 d . . . . .
H12 H 0.7835(16) 0.4702(7) 1.0524(12) 0.030(3) Uiso 1 1 d . . . . .
H13 H 0.6750(16) 0.3594(8) 0.9798(11) 0.033(3) Uiso 1 1 d . . . . .
H17A H 0.4749(15) 0.2718(7) 0.8928(11) 0.026(3) Uiso 1 1 d . . . . .
H17B H 0.4184(17) 0.2504(8) 0.7655(12) 0.034(3) Uiso 1 1 d . . . . .
H18 H 0.6605(16) 0.1781(7) 0.9275(11) 0.031(3) Uiso 1 1 d . . . . .
H19 H 0.9136(17) 0.1264(8) 0.8907(13) 0.037(3) Uiso 1 1 d . . . . .
H20 H 1.0567(17) 0.1678(8) 0.7292(12) 0.036(3) Uiso 1 1 d . . . . .
H21 H 0.9516(18) 0.2589(8) 0.6076(13) 0.041(4) Uiso 1 1 d . . . . .
H22 H 0.7069(17) 0.3123(8) 0.6426(12) 0.035(3) Uiso 1 1 d . . . . .
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'
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 O1 C1 115.05(6) . . ?
C15 O4 C16 115.86(6) . . ?
C8 N1 C14 108.79(5) . . ?
C8 N1 C17 126.49(6) . . ?
C14 N1 C17 124.52(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C5 112.75(6) . . ?
O2 C2 O1 122.95(6) . . ?
O2 C2 C5 124.29(6) . . ?
C4 C3 C8 120.06(6) . . ?
C4 C3 C9 133.32(6) . . ?
C8 C3 C9 106.62(5) . . ?
C3 C4 C5 118.85(6) . . ?
C3 C4 H4 120.0(8) . . ?
C5 C4 H4 121.1(8) . . ?
C4 C5 C2 117.06(5) . . ?
C4 C5 C6 120.64(6) . . ?
C6 C5 C2 122.29(6) . . ?
C5 C6 H6 117.9(8) . . ?
C7 C6 C5 121.49(6) . . ?
C7 C6 H6 120.6(8) . . ?
C6 C7 C8 117.30(6) . . ?
C6 C7 H7 119.9(9) . . ?
C8 C7 H7 122.8(9) . . ?
N1 C8 C3 108.97(5) . . ?
N1 C8 C7 129.40(6) . . ?
C7 C8 C3 121.64(6) . . ?
C10 C9 C3 133.43(6) . . ?
C10 C9 C14 120.03(6) . . ?
C14 C9 C3 106.54(5) . . ?
C9 C10 C11 118.73(6) . . ?
C9 C10 H10 122.4(7) . . ?
C11 C10 H10 118.9(7) . . ?
C10 C11 C12 120.63(6) . . ?
C10 C11 C15 117.07(6) . . ?
C12 C11 C15 122.30(6) . . ?
C11 C12 H12 118.8(8) . . ?
C13 C12 C11 121.54(6) . . ?
C13 C12 H12 119.6(8) . . ?
C12 C13 C14 117.33(6) . . ?
C12 C13 H13 121.6(8) . . ?
C14 C13 H13 121.1(8) . . ?
N1 C14 C9 109.06(6) . . ?
N1 C14 C13 129.21(6) . . ?
C13 C14 C9 121.73(6) . . ?
O3 C15 O4 122.93(6) . . ?
O3 C15 C11 124.10(7) . . ?
O4 C15 C11 112.97(6) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C23 112.99(5) . . ?
N1 C17 H17A 108.1(8) . . ?
N1 C17 H17B 106.9(8) . . ?
C23 C17 H17A 110.5(8) . . ?
C23 C17 H17B 109.6(8) . . ?
H17A C17 H17B 108.6(11) . . ?
C19 C18 C23 120.62(6) . . ?
C19 C18 H18 121.2(8) . . ?
C23 C18 H18 118.2(8) . . ?
C18 C19 C20 119.95(7) . . ?
C18 C19 H19 120.3(9) . . ?
C20 C19 H19 119.8(9) . . ?
C19 C20 C21 119.65(7) . . ?
C19 C20 H20 120.8(9) . . ?
C21 C20 H20 119.5(9) . . ?
C20 C21 C22 120.39(7) . . ?
C20 C21 H21 121.7(9) . . ?
C22 C21 H21 117.9(9) . . ?
C21 C22 H22 119.0(8) . . ?
C23 C22 C21 119.96(7) . . ?
C23 C22 H22 121.0(8) . . ?
C18 C23 C17 119.57(6) . . ?
C18 C23 C22 119.41(6) . . ?
C22 C23 C17 121.02(6) . . ?
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 C1 1.4427(9) . ?
O1 C2 1.3413(8) . ?
O2 C2 1.2154(8) . ?
O3 C15 1.2160(9) . ?
O4 C15 1.3414(9) . ?
O4 C16 1.4469(9) . ?
N1 C8 1.3862(8) . ?
N1 C14 1.3864(8) . ?
N1 C17 1.4525(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C5 1.4816(9) . ?
C3 C4 1.3896(8) . ?
C3 C8 1.4186(9) . ?
C3 C9 1.4449(9) . ?
C4 C5 1.3937(9) . ?
C4 H4 0.954(14) . ?
C5 C6 1.4130(9) . ?
C6 C7 1.3912(9) . ?
C6 H6 1.018(13) . ?
C7 C8 1.4019(9) . ?
C7 H7 0.945(16) . ?
C9 C10 1.3914(9) . ?
C9 C14 1.4177(9) . ?
C10 C11 1.3971(9) . ?
C10 H10 1.059(13) . ?
C11 C12 1.4106(9) . ?
C11 C15 1.4847(9) . ?
C12 C13 1.3915(9) . ?
C12 H12 1.008(14) . ?
C13 C14 1.3998(9) . ?
C13 H13 0.986(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C23 1.5120(9) . ?
C17 H17A 0.967(12) . ?
C17 H17B 0.998(14) . ?
C18 C19 1.3923(10) . ?
C18 C23 1.3942(9) . ?
C18 H18 0.991(13) . ?
C19 C20 1.3926(12) . ?
C19 H19 0.993(15) . ?
C20 C21 1.3933(12) . ?
C20 H20 0.956(14) . ?
C21 C22 1.3963(11) . ?
C21 H21 0.965(15) . ?
C22 C23 1.3951(10) . ?
C22 H22 1.036(14) . ?
